[4+1]、[5+1]和[4+2]关环法合成锇呋喃、锇萘和锇吡啶
|
摘要
金属杂芳香化学是芳香化学与金属有机化学之间相互交叉产生的一个新的研究领域。近年来，由于金属杂芳香化合物具有潜在特殊的光、电、磁学性质而日益引起科学家的关注。此类化合物不仅具有芳香化合物的特点，如环状，共轭，平面结构，低场化学位移，而且由于金属碳(M-C)多重键的存在，还具有金属有机化合物的反应性。目前已知的种类主要有：金属苯，金属苯炔，金属吡啶，金属吡哺鎓，硫杂金属苯，金属吡咯，金属呋喃，金属噻吩，金属萘，金属萘炔，金属苯并呋喃等。其中对金属杂稠环芳烃(金属萘，金属萘炔等)以及部分含其它杂原子的金属杂芳香化合物(金属吡啶等)的研究较少。本文主要研究了金属试剂OsCl_2(PPh_3)_3与炔醇配体HC≡CCH(OH)Ph的反应：通过[4+1]环化法合成出了锇呋喃化合物；通过[5+1]环化法合成出了首例金属萘二聚体以及第二例金属萘炔；首次发现了金属杂1，3-丁二烯与腈类的[4+2]环加成反应，得到首例后过渡系金属吡啶及其衍生物金属吡啶盐。本文主要分为以下五个部分：
第一章是绪论，介绍了金属杂芳香化合物的研究现状。从中可以看出，该领域目前的研究重点仍然是合成新颖的金属杂芳香化合物，其中对金属苯的高级同系物(金属萘，金属萘炔等)，以及部分含主族杂原子(氮，氧，硫等)的金属杂芳香化合物(金属吡啶)的研究相对较少。基于此研究现状，结合本实验室研究特色，提出了利用[4+1]法合成金属呋喃，[5+1]法合成金属萘以及[4+2]环加成法合成金属吡啶的思路。
第二章研究了金属试剂OsCl_2(PPh_3)_3与炔醇配体HC≡CCH(OH)Ph的反应，得到了羟基分子内配位的环状锇乙烯基化合物2-1(Scheme 1)。研究了该化合物的反应性(Scheme 2)，发现在加热或碱的作用下2-1可以转化为锇呋喃化合物2-2和2-3。这可以看做是[4+1]环化法在合成金属呋喃方面的应用。2-1与CO以及DPPB(Ph_2P(CH_2)_4PPh_2)反应分别得到锇乙烯基化合物2-4和2-5。
第三章主要研究了含金属氢的锇卡拜化合物3-2的合成及其反应性(Scheme3)，利用金属氢向卡拜碳原子的迁移反应以及苯基的C-H活化，选择性的合成出了首例金属萘二聚体3-3及第二例金属萘炔3-4。并且实现了金属萘向金属萘炔的转化，这也可以看做首例金属苯向金属苯炔的转化，为合成金属苯炔提供了一种具有潜在应用价值的合成方法。另外，3-2还可以与H_2O发生[4+1]环化反应得到羟基分子内配位的环状锇乙烯基化合物3-5(Scheme 4)。
第四章研究了化合物3-2与乙腈的反应(Scheme 5)。发现它们之间可以发生形式上的[4+2]环加成反应得到首例后过渡系金属吡啶4-2，及其衍生物金属吡啶盐4-1。化合物4-1和4-2具有顺磁性，这在其他金属杂芳香化合物的研究中未见报道。化合物4-1还可以与H_2O发生亲核加成反应得到氮、锇杂环己二烯化合物4-3(Scheme 6)。类似的反应在金属杂芳香化学中仅有两例(同一篇报道)。
第五章总结了本论文的创新性，并对今后的研究工作进行了展望。
The chemistry of transition-metal-containing aromatic compounds is currentlyattracting wider research interests because they can display both the reactivitiesrelated to organometallic compounds and the aromatic properties including ringplanarity,low chemical shift.Previous study has led to the isolation andcharacterization of an impressive number of transition-metal-containing aromaticcompounds including metallabenzene,metallabenzyne,metallapyridine,metallapyrylium,metallathiabenzene,metallapyrrole,metallafuran,metallathiophene,metallanaphthalene,metallanaphthalyne and metallabenzofurans.Among them,themetallanaphthalene,metallanaphthalyne,and the hetero-atom containingmetallaaromatics such as metallapyridine are very rare.In this dissertation,theresearch was carried out based on the reaction between OsCl_2(PPh_3)_3 andHC≡CCH(OH)Ph.The osmafurans were synthesized by[4+1]cyclization reaction.The[5+1]cyclization reaction was successfully used in the synthesis ofmetallanaphthalene and metallanaphthalyne.The first formal[4+2]cycloadditionreaction between hydride osmium alkenylcarbyne and acetonitrile afforded the firstlate-transition-metal-containing metallapyridine and its derivative metallapyridinium.
This dissertation contains five chapters.
In chapter 1,the research background of transition-metal-containing aromatics wasreviewed.On of the major issues of this field is the synthesis of novel aromaticmetallacycles.In this regard,some strategies were proposed based on the previouswork of our group,including constructing metallafuran by[4+1]cyclization,metallanaphthalene and metallanaphthalyne by[5+1]cyclization,and metallapyridineby[4+2]cycloaddition reaction,respectively.
In chapter 2,the reaction between OsCl_2(PPh_3)_3 and HC≡CCH(OH)Ph wasinvestigated,giving the osmium vinyl complex 2-1 (Scheme 1) with intramolecularcoordinated hydroxyl group.The reactivity of 2-1 was investigated (Scheme 2) andthe metallafurans 2-2 and 2-3 were synthesized by heating the DCE (ClCH_2CH_2Cl) solution of 2-1 under reflux and treating 2-1 with Cs_2CO_3,respectively.Thecompound 2-1 can also react with CO and DPPB to give osmium vinyl compound 2-4and 2-5,respectively.
In chapter 3,the hydride osmium alkenylcarbyne compound 3-2 was synthesizedfrom the reaction of 2-1 and HBF_4 (Scheme 3).The first metallanaphthalene dimmer3-3 and the second metallanaphthalyne 3-4 can be selectively synthesized from 3-2 via intramolecular C-H activation of phenyl (Scheme 3).Furthermore,thetransformation of 3-3 to 3-4 represented the first example of the conversion ofmetallabenzene to metallabenzyne,providing a potentially useful synthetic method forthe formation of metallabenzyne.Interestingly,3-2 can also react with H_2O in thepresence of AgBF_4,CO via the formal[4+1]cyclization to give the osmium vinylcompound 3-5 (Scheme 4) with intramolecular coordinated hydroxyl group.
In Chapter 4,the formal[4+2]cycloaddition reaction between the hydride osmiumalkenylcarbyne 3-2 and acetonitrile was firstly reported,affording the firstlate-transition-metal-containing metallapyridine 4-2 (Scheme 5) and its derivativemetallapyridinium 4-1.The paramagnetism of 4-1 and 4-2 is unprecedented in thechemistry of transition-metal-containing aromatic compounds.The osmapyridinium4-1 can also undergo aromatic nucleophilic addition reaction with H_2O (Scheme 6).This reaction pattern is also very rare in the chemistry of aromatic metallacycles.
In chapter 5,the innovation of this dissertation was summarized and the prospect ofthis research is presented.
第一章是绪论，介绍了金属杂芳香化合物的研究现状。从中可以看出，该领域目前的研究重点仍然是合成新颖的金属杂芳香化合物，其中对金属苯的高级同系物(金属萘，金属萘炔等)，以及部分含主族杂原子(氮，氧，硫等)的金属杂芳香化合物(金属吡啶)的研究相对较少。基于此研究现状，结合本实验室研究特色，提出了利用[4+1]法合成金属呋喃，[5+1]法合成金属萘以及[4+2]环加成法合成金属吡啶的思路。
第二章研究了金属试剂OsCl_2(PPh_3)_3与炔醇配体HC≡CCH(OH)Ph的反应，得到了羟基分子内配位的环状锇乙烯基化合物2-1(Scheme 1)。研究了该化合物的反应性(Scheme 2)，发现在加热或碱的作用下2-1可以转化为锇呋喃化合物2-2和2-3。这可以看做是[4+1]环化法在合成金属呋喃方面的应用。2-1与CO以及DPPB(Ph_2P(CH_2)_4PPh_2)反应分别得到锇乙烯基化合物2-4和2-5。
第三章主要研究了含金属氢的锇卡拜化合物3-2的合成及其反应性(Scheme3)，利用金属氢向卡拜碳原子的迁移反应以及苯基的C-H活化，选择性的合成出了首例金属萘二聚体3-3及第二例金属萘炔3-4。并且实现了金属萘向金属萘炔的转化，这也可以看做首例金属苯向金属苯炔的转化，为合成金属苯炔提供了一种具有潜在应用价值的合成方法。另外，3-2还可以与H_2O发生[4+1]环化反应得到羟基分子内配位的环状锇乙烯基化合物3-5(Scheme 4)。
第四章研究了化合物3-2与乙腈的反应(Scheme 5)。发现它们之间可以发生形式上的[4+2]环加成反应得到首例后过渡系金属吡啶4-2，及其衍生物金属吡啶盐4-1。化合物4-1和4-2具有顺磁性，这在其他金属杂芳香化合物的研究中未见报道。化合物4-1还可以与H_2O发生亲核加成反应得到氮、锇杂环己二烯化合物4-3(Scheme 6)。类似的反应在金属杂芳香化学中仅有两例(同一篇报道)。
第五章总结了本论文的创新性，并对今后的研究工作进行了展望。
The chemistry of transition-metal-containing aromatic compounds is currentlyattracting wider research interests because they can display both the reactivitiesrelated to organometallic compounds and the aromatic properties including ringplanarity,low chemical shift.Previous study has led to the isolation andcharacterization of an impressive number of transition-metal-containing aromaticcompounds including metallabenzene,metallabenzyne,metallapyridine,metallapyrylium,metallathiabenzene,metallapyrrole,metallafuran,metallathiophene,metallanaphthalene,metallanaphthalyne and metallabenzofurans.Among them,themetallanaphthalene,metallanaphthalyne,and the hetero-atom containingmetallaaromatics such as metallapyridine are very rare.In this dissertation,theresearch was carried out based on the reaction between OsCl_2(PPh_3)_3 andHC≡CCH(OH)Ph.The osmafurans were synthesized by[4+1]cyclization reaction.The[5+1]cyclization reaction was successfully used in the synthesis ofmetallanaphthalene and metallanaphthalyne.The first formal[4+2]cycloadditionreaction between hydride osmium alkenylcarbyne and acetonitrile afforded the firstlate-transition-metal-containing metallapyridine and its derivative metallapyridinium.
This dissertation contains five chapters.
In chapter 1,the research background of transition-metal-containing aromatics wasreviewed.On of the major issues of this field is the synthesis of novel aromaticmetallacycles.In this regard,some strategies were proposed based on the previouswork of our group,including constructing metallafuran by[4+1]cyclization,metallanaphthalene and metallanaphthalyne by[5+1]cyclization,and metallapyridineby[4+2]cycloaddition reaction,respectively.
In chapter 2,the reaction between OsCl_2(PPh_3)_3 and HC≡CCH(OH)Ph wasinvestigated,giving the osmium vinyl complex 2-1 (Scheme 1) with intramolecularcoordinated hydroxyl group.The reactivity of 2-1 was investigated (Scheme 2) andthe metallafurans 2-2 and 2-3 were synthesized by heating the DCE (ClCH_2CH_2Cl) solution of 2-1 under reflux and treating 2-1 with Cs_2CO_3,respectively.Thecompound 2-1 can also react with CO and DPPB to give osmium vinyl compound 2-4and 2-5,respectively.
In chapter 3,the hydride osmium alkenylcarbyne compound 3-2 was synthesizedfrom the reaction of 2-1 and HBF_4 (Scheme 3).The first metallanaphthalene dimmer3-3 and the second metallanaphthalyne 3-4 can be selectively synthesized from 3-2 via intramolecular C-H activation of phenyl (Scheme 3).Furthermore,thetransformation of 3-3 to 3-4 represented the first example of the conversion ofmetallabenzene to metallabenzyne,providing a potentially useful synthetic method forthe formation of metallabenzyne.Interestingly,3-2 can also react with H_2O in thepresence of AgBF_4,CO via the formal[4+1]cyclization to give the osmium vinylcompound 3-5 (Scheme 4) with intramolecular coordinated hydroxyl group.
In Chapter 4,the formal[4+2]cycloaddition reaction between the hydride osmiumalkenylcarbyne 3-2 and acetonitrile was firstly reported,affording the firstlate-transition-metal-containing metallapyridine 4-2 (Scheme 5) and its derivativemetallapyridinium 4-1.The paramagnetism of 4-1 and 4-2 is unprecedented in thechemistry of transition-metal-containing aromatic compounds.The osmapyridinium4-1 can also undergo aromatic nucleophilic addition reaction with H_2O (Scheme 6).This reaction pattern is also very rare in the chemistry of aromatic metallacycles.
In chapter 5,the innovation of this dissertation was summarized and the prospect ofthis research is presented.
引文
[1] Bleeke J R, Aromatic Iridacycles[J], Ace. Chem. Res. 2007, 40(10): 1035-1047.
[2] Wright L J, Metallabenzenes and metallabenzenoids[J], Dalton Trans. 2006, (15):1821-1827.
[3] Landorf C W, Haley M M, Recent Advances in Metallabenzene Chemistry[J],Angew. Chem. Int. Ed. 2006,45(24): 3914-3936.
[4] Bleeke J R, Metallabenzenes [J], Chem. Rev. 2001, 101(5): 1205-1227.
[5] Jia G, Progress in the Chemistry of Metallabenzynes[J], Ace. Chem. Res. 2004,37(7): 479-486.
[6] Jia G, Recent progress in the chemistry of osmium carbyne and metallabenzyne complexes[J], Coord. Chem. Rev. 2007,251(17-20): 2167-2187.
[7] Weller K J, Filippov I, Briggs P M, Wigley D E, Pyridine Degradation Intermediates as Models for Hydrodenitrogenation Catalysis: Preparation and Properties of a Metallapyridine Complex[J], Organometallics 1998,17(3): 322-329.
[8] Bleeke J R, Blanchard J M B, Synthesis and Reactivity of a Metallapyrylium[J], J.Am. Chem. Soc. 1997, 119(23): 5443-5444.
[9] Bleeke J R, Hinkle P V, Rath N P, Synthesis, Structure, Spectroscopy, and Reactivity of a Metallathiabenzene[J], J. Am. Chem. Soc. 1999, 121(3): 595-596.
[10] Bianchini C, Meli A, Peruzzini M, Vizza F, Frediani P, Herrera V,Sanchez-Delgado R A, Opening, Desulfurization, and Hydrogenation of Thiophene at Iridium. An Experimental Study in a Homogeneous Phase[J], J. Am. Chem. Soc. 1993,115(7): 2731-2742.
[11] Chen J, Daniels L M, Angelici R J, New Modes of Thiophene Coordination and Reactivity: Structures of Cp~*Ir(η~2-thiophene), an Iridathiabenzene, and C~*Ir(η~4-thiophene·BH_3)[J], J.Am. Chem. Soc. 1990, 112(1): 199-204.
[12] Baya M, Esteruelas M A, Gonz(?)lez A I, L(?)pez A M, O(?)ate E, Formation of Azabutadienyl Fragments by Addition of the Isopropenyl Substituent of a Phosphine to Benzonitriles, Promoted by an Osmium Center[J], Organometallics 2005, 24(6):1225-1232.
[13]Bolano T,Castarlenas R,Esteruelas M A,Onate E,Assembly of an Allenylidene Ligand,a Terminal Alkyne,and an Acetonitrile Molecule:Formation of Osmacyclopentapyrrole Derivatives[J],J.Am.Chem.Soc.2006,128(12):3965-3973.
[14]Legzdins P,Lumb S A,Trapping of Cp*W(NO)(η~2-PhC≡CH),the KeyIntermediate in the C-H Activation of Alkanes byCp*W(NO)(CH_2SiMe_3)(CPh=CH_2)[J],Organometallics 1997,16(9):1825-1827.
[15]Alvarado Y,Daff P J,Perez P J,Poveda M L,Sanchez-Delgado R,Carmona E,Iridapyrrole Complexes via Formal 3 + 2 Cycloaddition of Iridium Alkenyls to Acetonitrile[J],Organometallics 1996,15(9):2192-2194.
[16]Bleeke J R,Putprasert P,Thananatthanachon T,Synthesis and Characterization of Fused-Ring Iridapyrroles[J],Organometallics 2008,27(22):5744-5747.
[17]Esteruelas M A,Masamunt A B,Olivan M,Onate E,Valencia M,Aromatic Diosmatricyclic Nitrogen-Containing Compounds[J],J.Am.Chem.Soc.2008,130(35):11612-11613.
[18]Bleeke J R,New P R,Blanchard J M B,Haile t,Beatty A M,Synthesis of a New Family of Metallafurans from (Oxapentadienyl)metal Precursors[J],Organometallics 1995,14(11):5127-5137.
[19]DeShong P,Sidler D R,Rybczynski P J,Slough G A,Rheingold A L,A General Method for the Preparation of Carbonyl Compounds and Butenolides from Organomanganese Pentacarbonyl Complexes[J],J.Am.Chem.Soc.1988,110(8):2575-2585.
[20]Davidson J L,Green M,Nyathi J C,Scott C,Stone F G A,Welch A J,Woodward P,Reactions of acyl-and alkyl-(tricarbonyl)(η~5-cyclopentadienyl)-molybdenum and -tungsten complexes with but-2-yne;molecular structures of [Mo(CO)(ButNC)(η~3- {O-C(O)-CMe-CMe-CMe})(η~5-C_5H_5)]and [MO-C(O)-C(Me){C(Me)}_2C(Me)-C(CF_3)-O(CO)(η~5-C_5H_5)][J],J.Chem.Soc.,Chem.Commun.1976,(18):714-715.
[21]Booth B L,Hargreaves R G,Reactions between methyl-,acetyl-,and phenylpentacarbonylmanganese and acetylenes[J],J.Chem.Soc.(A) 1970,(2):308-314.
[22] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4(CO)(PiPr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)(η~2-H_2)(CO)(P/Pr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993,12(3): 663-670.
[23] Werner H, Weinand R, Otto H, Aromaten(phosphan)metall-komplexe: XI. Funfgliedrige osmaheterocyclen durch alkin-insertion in eine Os-I oder Os-H-bindung[J], J. Organomet. Chem. 1986, 307(1): 49-59.
[24] Herrmann W A, Ziegler M L, Serhadll O, Organometallic Chemistry of Reactive Organic Compounds. 41. Metal-Induced Carbyne/Carbene Coupling with Buchner's Diazo Compound[J], Organometallics 1983,2(8): 958-962.
[25] Komiya S, Ito T, Cowie M, Yamamoto A, Ibers J A, Carbon-Hydrogen Bond Activation by Transition Metal Complexes. Oxidative Addition of Alkyl Methacrylate to Ruthenium. The Structure of Hydrido(2-n-butoxycarbonylpropenyl-C~1,O) tris(triphenylphosphine)ruthenium(Ⅱ)[J], J. Am. Chem. Soc. 1976, 98(13):3874-3884.
[26] Sunley G J, Menanteau P d C, Adams H, Bailey N A, Maitlis P M,Cyclometallation of Unsaturated Carboxylic Acids by Pentamethylcyclopentadienyl-rhodium and -iridium Complexes. Crystal Structures of [(C5Me5)Ir(CPh=CHCO-O)(Me2SO)] and [(C5Me5)Ir(CPh=CHCO-OMe)I]+[J], J.Chem. Soc, Dalton Trans. 1989, (12): 2415-2421.
[27] Castarlenas R, Esteruelas M A, Martin M, Oro L A, C-H activation of methyl vinyl ketone in Ir(acac)[η~2-CH_2=CHC(O)CH_3](PCy_3)[J], J. Organomet. Chem. 1998,564(1-2): 241-247.
[28] Dirnberger T, Werner H, A Series of Hydrido(vinyl)iridium(Ⅲ) Complexes That Are Thermodynamically More Stable than Their Olefin Iridium(Ⅰ) Isomers[J],Organometallics 2005, 24(21): 5127-5139.
[29] Li X, Chen P, Faller J W, Crabtree R H, Cycloiridation of a, P-Unsaturated Ketones, Esters, and Acetophenone[J], Organometallics 2005, 24(20): 4810-4815.
[30] Lowe C, Shklover V, Berke H, Tetracarbonyl(triphenylpropenetriyl)rhenium. A Delocalized rhenacyclobutadiene[J], Organometallics 1991,10(9): 3396-3399.
[31] Padolik L L, Galluci J C, Wojcicki A, Fischer-Type Rhenacyclobutadiene Complexes: Synthesis, Structure, and Nucleophilic Addition/Substitution and Oxidation Reactions [J], J. Am. Chem. Soc. 1993,115(22): 9986-9996.
[32] Garrett K E, Sheridan J B, Pourreau D B, Feng W C, Geoffroy G L, Staley D L,Rheingold A L, Transient Generation of the Reactive Carbene Complex [Cp(CO)_2W=CH(Tol)]~+ and Its Reactions with Alkynes To Form Vinylcarbene, Allyl,Naphthol, Diene, and Metallafuran Complexes[J], J. Am. Chem. Soc. 1989, 111(22):8383-8391.
[33] Woodworm B E, Frohnapfel D S, White P S, Templeton J L, Formation of Derivative Carbyne Complexes from Tp'(CO)_2M = CCH_3 (M = Mo, W)[J],Organometallics 1998,17(9): 1655-1662.
[34] Grotjahn D B, Hoerter J M, Hubbard J L, Double C-H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(I) Using Alkynes. Synthesis of l,4-Dien-3-ones[J], J. Am. Chem. Soc. 2004,126(29): 8866-8867.
[35] Bruce M I, Hall B C, Skelton B W, White A H, Zaitseva N N, Oligomerisation of alkynes at a pentamethylcyclopentadienylruthenium centre[J], J. Chem. Soc, Dalton Trans. 2000, (14): 2279-2286.
[36] Lu G-L, Roper W R, Wright L J, Clark G R, A 2-iridathiophene from reaction between IrCl(CS)(PPh_3)_2 and Hg(CH=CHPh)_2[J], J. Organomet. Chem. 2005, 690(4):972-981.
[37] Bleeke J R, Ortwerth M F, Chiang M Y, Electrophilic Addition to an Iridathiacyclopentene Complex. Synthesis of the First Metallathiophene[J],Organometalllics 1993,12(4): 985-987.
[38] Bleeke J R, Ortwerth M F, Rohde A M, Thiapentadienyl-Iridium-Phosphine Chemistry[J], Organometallics 1995,14(6): 2813-2826.
[39] Paneque M, Posadas C M, Poveda M L, Rendon N, Salazar V, Onate E, Mereiter K, Formation of Unusual Iridabenzene and Metallanaphthalene Containing Electron-Withdrawing Substituents[J], J. Am. Chem. Soc. 2003,125(33): 9898-9899.
[40] Paneque M, Posadas C M, Poveda M L, Rendon N, Santos L L, Alvarez E,Salazar V, Mereiter K, Onate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity[J], Organometallics 2007,26(14): 3403-3415.
[41] Zhang H, Feng L, Gong L, Wu L, He G, Wen T, Yang F, Xia H, Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC=CCH(OH)C=CH[J],Organometallics 2007,26(10): 2705-2713.
[42] Clark G R, Johns P M, Roper W R, Wright L J, An Osmabenzofuran from Reaction between Os(PhC = CPh)(CS)(PPh3)2 and Methyl Propiolate and the C-Protonation of this Compound to Form a Tethered Osmabenzene[J],Organometallics 2006,25(7): 1771-1777.
[43] Thorn D L, Hoffman R, Delocalization in metallocycles[J], Nouv. J. Chim. 1979,3(1): 39-45.
[44] Elliott G P, Roper W R, Waters J M, Metallacyclohexatrienes or 'metallabenzenes.' Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)(CO)(PPh_3)_2][J], J. Chem. Soc, Chem. Commun. 1982, (14):811-813.
[45] Iron M A, Lucassen A C B, Cohen H, Boom M E V d, Martin J M L, A Computational Foray into the Formation and Reactivity of Metallabenzenes [J], J. Am.Chem. Soc. 2004,126(37): 11699-11710.
[46] Alvarez E, Paneque M, Poveda M L, Rend(?)n N, Formation of Iridabenzenes by Coupling of Iridacyclopentadienes and Alkenes[J], Angew. Chem. Int. Ed. 2006,45(3):474-477.
[47] Chin C S, Lee H, New Iridacyclohexadienes and Iridabenzenes by [2+2+1] Cyclotrimerization of Alkynes and Facile Interconversion between Iridacyclohexadienes and Iridabenzenes [J], Chem. Eur. J. 2004, 10(18): 4518-4522.
[48] Chin C S, Lee H, Eum M-S, Iridabenzenes from Iridacyclopentadienes: Unusual C-C Bond Formation between Unsaturated Hydrocarbyl Ligands[J], Organometallics 2005, 24(20): 4849-4852.
[49] Bleeke J R, Peng W-J, Synthesis, Structure, and Spectroscopy of Iridacyclohexadiene Complexes[J], Organometallics 1987, 6(7): 1576-1578.
[50] Bleeke J R, Xie Y-F, Peng W-J, Chiang M, Metallabenzene: Synthesis, Structure,and Spectroscopy of a l-Irida-3,5-dimethylbenzene Complex[J], J. Am. Chem. Soc. 1989,111(11):4118-4120.
[51]Gilbertson R D,Weakley T J R,Haley M M,Direct Synthesis of an Iridabenzene from a Nucleophilic 3-Vinyl-l-cyclopropene[J],J.Am.Chem.Soc.1999,121(11):2597-2598.
[52]Gilbertson R D,Weakley T J R,Haley M M,Synthesis,Characterization,and Isomerization of an Iridabenzvalene[J],Chem.Eur.J.2000,6(3):437-441.
[53]Wu H-P,Lanza S,Weakley T J R,Haley M M,Metallabenzenes and Valence Isomers.3.Unexpected Rearrangement of Two Regioisomeric Iridabenzenes to an (η~5-Cyclopentadienyl)iridium(Ⅰ) Complex[J],Organometallics 2002,21(14):2824-2826.
[54]Gilbertson R D,Lau T L S,Lanza S,Wu H-P,Weakley T J R,Haley M M,Synthesis,Spectroscopy,and Structure of a Family of Iridabenzenes Generated by the Reaction of Vaska-Type Complexes with a Nucleophilic 3-Vinyl-1-cyclopropene[J],Organometallics 2003,22(16):3279-3289.
[55]Wu H-P,Weakley T J R,Haley M M,Regioselective Formation of β-Alkyl-α-phenyliridabenzenes via Unsymmetrical 3-Vinylcyclopropenes:Probing Steric and Electronic Influences by Varying the Alkyl Ring Substituent[J],Chem.Eur.J.2005,11(4):1191-1200.
[56]Jacob V,Weakley T J R,Haley M M,Metallabenzenes and Valence Isomers.Synthesis and Characterization of a Platinabenzene[J],Angew.Chem.Int.Ed.2002,41 (18):3470-3473.
[57]Landorf C W,Jacob V,Weakley T J R,Haley M M,Rational Synthesis of Platinabenzenes[J],Organometallics 2004,23(6):1174-1176.
[58]Xia H,He G,Zhang H,Wen T B,Sung H H Y,Williams I D,Jia G,Osmabenzenes from the Reactions of HC ≡ CCH(OH)C ≡CH with OsX_2(PPh_3)_3 (X =Cl,Br)[J],J.Am.Chem.Soc.2004,126(22):6862-6863.
[59]Zhang H,Wu L,Lin R,Zhao Q,He G,Yang F,Wen T B,Xia H,Synthesis,Characterization and Electrochemical Properties of Stable Osmabenzenes Containing PPh3 Substituents[J],Chem.Eur.J.2009,15(14):3546-3559.
[60]Zhang H,Xia H,He G,Wen T B,Gong L,Jia G,Synthesis and Characterization of Stable Ruthenabenzenes[J], Angew. Chem. Int. Ed. 2006,45(18): 2920-2923.
[61] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[62] Gong L, Chen Z, Lin Y, He X, Wen T B, Xu X, Xia H, Osmabenzenes from Osmacycles Containing an η~2-Coordinated Olefin[J], Chem. Eur. J. 2009, 15(25):6258-6266.
[63] Wen T B, Zhou Z Y, Jia G, Synthesis and Characterization of a Metallabenzyne[J],Angew. Chem. Int. Ed. 2001,40(10): 1951-1954.
[64] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[65] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006, 128(2): 13742-13752.
[66] Bierstedt A, Clark G R, Roper W R, Wright L J, A 2-iridafuran from reaction between a 1-iridaindene and methyl propiolate[J], J. Organomet. Chem. 2006,691(18): 3846-3852.
[67] Bruce M I, Hall B C, Skelton B W, Tiekink E R T, White A H, Zaitseva N N,Some Pentamethylcyclopentadienyl-Ruthenium Derivatives of Methyl Propiolate[J],Aust. J. Chem. 2000, 53(2): 99-107.
[68] Grossmann U, Hund H-U, Bosch H W, Schmalle H, Berke H, Trimerisierung von Propiols(?)uremethylester an Dicarbonylbis (phosphordonor)eisen-Komplexen[J], J.Organomet. Chem. 1991, 408(2): 203-218.
[69] Birk R, Grossmann U, Hund H-U, Berke H, Koordination und Chemie von Acetylenen an dicarbonylbis (tirmethlphosphit)eisen-fragmenten[J], J. Organomet.Chem. 1988, 345(3): 321-329.
[70] Yamazaki H, Aoki K, A novel six-membered ruthenium metallocycle [J], J. Organomet.Chem.1976,122(3):C54-C58.
[1]Xia H,He G,Zhang H,Wen T B,Sung H H Y,Williams I D,Jia G,Osmabenzenes from the Reactions of HC≡CCH(OH)C≡CH with OsX_2(PPh_3)_3 (X=Cl,Br)[J],J.Am.Chem.Soc.2004,126(22):6862-6863.
[2]Zhang H,Wu L,Lin R,Zhao Q,He G,Yang F,Wen T B,Xia H,Synthesis,Characterization and Electrochemical Properties of Stable Osmabenzenes Containing PPh3 Substituents[J],Chem.Eur.J.2009,15(14):3546-3559.
[3]Gong L,Lin Y,Wen T B,Zhang H,Zeng B,Xia H,Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J],Organometallics 2008,27(11):2584-2589.
[4]Gong L,Chen Z,Lin Y,He X,Wen T B,Xu X,Xia H,Osmabenzenes from Osmacycles Containing an η~2-Coordinated Olefin[J],Chem.Eur.J.2009,15(25):6258-6266.
[5]Zhang H,Xia H,He G,Wen T B,Gong L,Jia G,Synthesis and Characterization of Stable Ruthenabenzenes[J],Angew.Chem.Int.Ed.2006,45(18):2920-2923.
[6]Zhang H,Feng L,Gong L,Wu L,He G,Wen T,Yang F,Xia H,Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC≡CCH(OH)C≡CH[J],Organometallics 2007,26(10):2705-2713.
[7]Shilov A E,Shul'pin G B,Activation of C-H bonds by Metal Complexes[J],Chem.Rev.1997,97(8):2879-2932.
[8]Wemer H,Esteruelas M A,Otto H,Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr_3)_2 (M = Ru,Os) with Alkynes.The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)_2[J],Organometallics 1986,5(11):2295 -2299.
[9]Gong L,Lin Y,He G,Zhang H,Wang H,Wen T B,Xia H,Synthesis and Characterization of an Air-Stable p-Osmaphenol[J],Organometallics 2008,27(3):309-311.
[10]Esteruelas M A,Garc(?)a-Yebra C,Oliv(?)n M,O(?)ate E,Tajada M A,The Dihydride-Osmium(Ⅳ) Complex [OsH_2(κ~2-O_2CCH_3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[11] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4( CO) (P/Pr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)( η~2-H_2)(CO)(P/Pr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993,12(3): 663-670.
[12] Buil M L, Esteruelas M A, Garc(?)a-Yebra C, Gutierrez-Puebla E, Olivan M,Hydride-Hydroxyosmacyclopropene versus Hydride-Hydroxycarbyne and Cyclic Hydroxycarbene: Influence of the Substituents at the C(OH) Carbon Atom of the Carbon Donor Ligand[J], Organometallics 2000, 19(11): 2184-2193.
[13] Rickard C E F, Roper W R, Williamson A, Wright L J, Exchange of boryl ligand substituents in Os[B(OEt)_2]Cl(CO)(PPh_3)_2[J], J. Organomet. Chem. 2004, 689(9):1609-1616.
[14] Esteruelas M A, Lahoz F J, O(?)ate E, Oro L A, Zeier B, Reactions of OsHCl(CO)(PiPr_3)_2 with Alkynl-1-ols: Synthesis of (Vinylcarbene)osmium(Ⅱ) Complexes[J], Organometallics 1994, 13(5): 1662-1668.
[15] Hoffmann P R, Caulton K G, Solution structure and dynamics of five-coordinated d6 complexes[J], J. Am. Chem. Soc. 1975, 97(15): 4221-4228.
[1] Bleeke J R, Aromatic Iridacycles[J], Acc. Chem. Res. 2007,40(10): 1035-1047.
[2] Wright L J, Metallabenzenes and metallabenzenoids[J], Dalton Trans. 2006, (15):1821-1827.
[3] Landorf C W, Haley M M, Recent Advances in Metallabenzene Chemistry [J],Angew. Chem. Int. Ed. 2006,45(24): 3914-3936.
[4] Bleeke J R, Metallabenzenes [J], Chem. Rev. 2001,101(5): 1205-1227.
[5] Jia G, Recent progress in the chemistry of osmium carbyne and metallabenzyne complexes[J], Coord. Chem. Rev. 2007,251(17-20): 2167-2187.
[6] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006,128(2): 13742-13752.
[7] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[8] Jia G, Progress in the Chemistry of Metallabenzynes [J], Acc. Chem. Res. 2004,37(7): 479-486.
[9] Wen T B, Ng S M, Hung W Y, Zhou Z Y, Lo M F, Shek L-Y, Williams I D, Lin Z,Jia G, Protonation and Bromination of an Osmabenzyne: Reactions Leading to the Formation of New Metallabenzynes[J], J. Am. Chem. Soc. 2003, 125(4): 884-885.
[10] Wen T B, Zhou Z Y, Jia G, Synthesis and Characterization of a Metallabenzyne[J],Angew. Chem. Int. Ed. 2001,40(10): 1951-1954.
[11] Paneque M, Posadas C M, Poveda M L, Rendon N, Salazar V, O(?)ate E, Mereiter K, Formation of Unusual Iridabenzene and Metallanaphthalene Containing Electron-Withdrawing Substituents[J], J. Am. Chem. Soc. 2003, 125(33): 9898-9899.
[12] Paneque M, Posadas C M, Poveda M L, Rendon N, Santos L L, (?)lvarez E,Salazar V, Mereiter K, Onate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity [J], Organometallics 2007, 26(14): 3403-3415.
[13] He G, Zhu J, Hung W Y, Wen T B, Sung H H-Y, Williams I D, Lin Z, Jia G, A Metallanaphthalyne Complex from Zinc Reduction of a Vinylcarbyne Complex [J],Angew. Chem. Int. Ed. 2007,46(47): 9065-9068.
[14] Esteruelas M A, Garc(?)a-Yebra C, Oliv(?)n M, O(?)ate E, Tajada M A, The Dihydride-Osmium(IV) Complex [OsH_2 (η~2-O_2CCH_3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[15] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4( CO) (P/Pr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)( κ~2-H_2)(CO)(PzPr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993, 12(3): 663-670.
[16] Werner H, Esteruelas M A, Otto H, Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr-3)_2 (M = Ru, Os) with Alkynes. The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)_2[J], Organometallics 1986, 5(11):2295-2299.
[17] Gong L, Lin Y, He G, Zhang H, Wang H, Wen T B, Xia H, Synthesis and Characterization of an Air-Stable p-Osmaphenol[J], Organometallics 2008, 27(3):309-311.
[18] Therrien B, Vieille-Petit L, S(?)ss-Fink G, X-ray crystallographic study of two dinuclear triply-bridged p-cymene osmium complexes[J], J. Mol. Struct. 2005,738(1-3): 161-163.
[19] Wen T B, Zhou Z Y, Lo M F, Williams I D, Jia G, Vinylidene, Allenylidene, and Carbyne Complexes from the Reactions of [OsCl_2(PPh_3)-3] with HC=CC(OH)Ph-2[J],Organometallics 2003,22(25): 5217-5225.
[20] Kuhlman R, Streib W E, Caulton K G, Protonation of Chloride in Os(H)_2Cl_2(P~iPr_3)_2: Synthesis of [ (P~iPr_3)_2H-2Os(μ-Cl)_3OsH_2(P~iPr-3)_2]CF_3SO-3[J], Inorg.Chem. 1995, 34(7): 1788-1792.
[21] Fanwick P E, Fraser I F, Tetrick S M, Walton R A, Multiply Bonded Octahalodiosmate(Ⅲ) Anions. 4. Reactions with Nitrogen and Phosphorus Donor Ligands That Lead to Cleavage of the Os=Os Bond[J], Inorg. Chem. 1987, 26(2):3786-3791.
[22] Bolano T, Castarlenas R, Esteruelas M A, Onate E, Hydride-Carbyne to Carbene Transformation in an Osmium-Acetate-Bis(triisopropylphosphine) System: Influence of the Coordination Mode of the Carboxylate and the Reaction Solvent[J],Organometallics 2007,26(8): 2037-2041.
[23] Bolano T, Castarlenas R, Esteruelas M A, Modrego F J, Onate E,Hydride-Alkenylcarbyne to Alkenylcarbene Transformation in Bisphosphine-Osmium complexes[J], J. Am. Chem. Soc. 2005,127(31): 11184-11195.
[24] Caulton K G, Factors governing the equilibrium between metal alkyl, alkylidene and alkylidyne: MCX_2R, X-M=CXR and X_2M=CR[J], J. Organomet. Chem. 2001,617-618,56-64.
[25] Spivak G J, Coalter J N, Oliv(?)n M, Eisenstein O, Caulton K G, Osmium Converts Terminal Olefins to Carbynes: α-Hydroge Migration Redox Isomers with Reversed Stability for Ruthenium and for Osmium[J], Organometallics 1998, 17(6): 999-1001.
[26] Pilar Barrio M A E a, Preparation and Characterization of an Isometallabenzene with the Structure of a l,2,4-Cyclohexatriene[J], J. Am. Chem. Soc. 2004, 126(7):1946-1947.
[27] Esteruelas M A, Gonzalez A I, Lopez A M, Onate E, An Osmium-Carbene Complex with Fischer-Schrock Ambivalent Behavior[J], Organometallics 2003, 22(3): 414-425.
[28] Furstner A, Davies P W, Alkyne metathesis [J], Chem. Commun. 2005, 18(5719):2307-2320.
[29] Bunz U H F, How Are Alkynes Scrambled[J], Science 2005, 308: 216-217.
[30] Zhang H, Feng L, Gong L, Wu L, He G, Wen T, Yang F, Xia H, Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC=CCH(OH)C=CH[J],Organometallics 2007, 26(10): 2705-2713.
[31] Rickard C E F, Roper W R, Woodgate S D, Wright L J, Electrophilic Aromatic Substitution Reactions of a Metallabenzene: Nitration and Halogenation of the Osmabenzene[Os[C(SMe)CHCHCHCH]I(CO)(PPh_3)_2][J], Angew. Chem. Int. Ed.2000, 39(4): 750-752.
[32] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[33] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006, 128(42): 13742-13752.
[34] Xia H, He G, Zhang H, Wen T B, Sung H H Y, Williams I D, Jia G,Osmabenzenes from the Reactions of HC=CCH(OH)C=CH with OsX-2(PPh_3)_3 (X =Cl, Br)[J], J. Am. Chem. Soc. 2004, 126(22): 6862-6863.
[35] Rickard C E F, Roper W R, Woodgate S D, Wright L J, Reaction between the thiocarbonyl complex, Os(CS)(CO)(PPh_3)_3, and propyne: crystal structure of a new sulfur-substituted osmabenzene[J], J. Organomet. Chem. 2001, 623: 109-115.
[36] Elliott G P, Roper W R, Waters J M, Metallacyclohexatrienes or 'metallabenzenes.' Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)(CO)(PPh-3)_2][J], J. Chem. Soc, Chem. Commun. 1982, (14):811-813.
[37] Cruickshank D W J, X-ray results on aromatic hydrocarbons [J], Tetrahedron 1962, 17(3-4): 155-161.
[38] Edwards A J, Willis A C, Wenger E, Reactions of Benzyne-Nickel(O) Complexes with Thioalkynes: Preparation and Coordination of Polydentate Thioethers Containing a 2,3-Naphthylene Backbone[J], Organometallics 2002,21(8): 1654-1661.
[39] Mashima K, Komura N, Yamagata T, Tani K, Synthesis and Crystal Structure of a Cationic Trinuclear Ruthenium(Ⅱ) complex, [Ru_3(μ_2-Cl)_3(μ_3-Cl)_2 [1,2-bis (diphenylphosphino)benzene}_3]PF-6[J], Inorg. Chem. 1997, 36(13): 2908-2912.
[40] Yeomans B D, Humphrey D G, Heath G A, Halide-birdged arsine- and phosphine-capped diruthenium complexes, [(R_3As)_3Ru(μ-X)_3Ru(AsR_3)_3]~+ and [(R_3P)_3Ru(μ-X)_3Ru(PR_3)_3]~+ (X = Cl or Br), as precursors to confacial mixed-valence ruthenium 'blues': spectroelectrochemical studies spanning the binuclear oxidation states Ⅱ,Ⅱ,Ⅱ,Ⅲ and Ⅲ,Ⅲ[J], J. Chem. Soc, Dalton Trans. 1997, (22): 4153-4166.
[41] Buil M L, Esteruelas M A, Garc(?)a-Yebra C, Guti(?)rrez-Puebla E, Olivan M,Hydride-Hydroxyosmacyclopropene versus Hydride-Hydroxycarbyne and Cyclic Hydroxycarbene: Influence of the Substituents at the C(OH) Carbon Atom of the Carbon Donor Ligand[J], Organometallics 2000,19(11): 2184-2193.
[42] Buil M L, Esteruelas M A, Goni E, Olivan M, Onate E, Displacement of Phenyl and Styryl Ligands by Benzophenone Imine and 2-Vinylpyridine on Ruthenium and Osmium[J], Organometallics 2006,25(12): 3076-3083.
[43] Castro-Rodrigo R, Esteruelas M A, Lopez A M, O(?)ate E, Reactions of a Dihydrogen Complex with Terminal Alkynes: Formation of Osmium-Carbyne and -Carbene Derivatives with the Hydridotris(pyrazolyl)borate Ligand[J],Organometallics 2008,27(14): 3547-3555.
[44] Rickard C E F, Roper W R, Williamson A, Wright L J, Exchange of boryl ligand substituents in Os[B(OEt)_2]Cl(CO)(PPh_3)_2[J], J. Organomet. Chem. 2004, 689(9):1609-1616.
[45] a) Stephens P J, Devlin F J, Chabalowski C F, Frisch M J, Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields[J], J. Phys. Chem. 1994, 98(45): 11623-11627; b) Becke A D,Density-functional thermochemistry. Ⅲ. The role of exact exchange[J], J. Chem. Phys.1993, 98(7): 5648-5652; c) Lee C, Yang W, Parr R G, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J], Phys. Rev. B. 1988, 37(2): 785-789.
[46] Couty M, Hall M B, Basis sets for transition metals: optimized outer p functions[J], J. Comput. Chem. 1996, 17(11): 1359-1370.
[47] Check C E, Faust T O, Bailey J M, Wright B J, Gilbert T M, Sunderlin L S,Addition of Polarization and Diffuse Functions to the LANL2DZ Basis Set for P-Block Elements[J], J. Phys. Chem. A. 2001,105(34): 8111-8116.
[48] Hay P J, Wadt W R, Ab initio Effective core potentials for molecular calculations.Potentials for potassium to gold including the outermost core orbitals[J], J. Chem.Phys. 1985, 82(1), 299-310.
[49] a) Petersson G A, Al-Laham M A, A complete basis set model chemistry. Ⅱ.Open-shell systems and the total energies of the first-row atoms[J], J. Chem. Phys.1991, 94(9): 6081-6090; b) Petersson G A, Bennett A, Tensfeldt T G, Al-Laham M A,Shirley W A, Mantzaris J, A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements[J], J. Chem. Phys. 1988,89(4): 2193-2218.
[50] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R,Montgomery J A, Vreven Jr, T, Kudin K N, Burant J C, Millam J M, Iyengar S S,Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A,Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P,Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O,Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A,Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C,Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q,Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P,Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A,Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A,Gaussian 03, Revision C. 02; Gaussian, Inc., Wallingford CT, 2004.
[1]Baya M,Esteruelas M A,Gonz(?)lez A I,L(?)pez A M,O(?)ate E,Formation of Azabutadienyl Fragments by Addition of the Isopropenyl Substituent of a Phosphine to Benzonitriles,Promoted by an Osmium Center[J],Organometallics 2005,24(6):1225-1232.
[2]Bolano T,Castarlenas R,Esteruelas M A,Onate E,Assembly of an Allenylidene Ligand,a Terminal Alkyne,and an Acetonitrile Molecule:Formation of Osmacyclopentapyrrole Derivatives[J],J.Am.Chem.Soc.2006,128(12):3965-3973.
[3]Legzdins P,Lumb S A,Trapping of Cp*W(NO)(η~2-PhC≡CH),the Key Intermediate in the C-H Activation of Alkanes by Cp*W(NO) (CH_2SiMe_3) (CPh=CH_2)[J],Organometallics 1997,16(9):1825-1827.
[4]Alvarado Y,Daff P J,Perez P J,Poveda M L,Sanchez-Delgado R,Carmona E,Iridapyrrole Complexes via Formal 3 + 2 Cycloaddition of Iridium Alkenyls toAcetonitrile[J],Organometallics 1996,15(9):2192-2194.
[5]Bleeke J R,Putprasert P,Thananatthanachon T,Synthesis and Characterization of Fused-Ring Iridapyrroles[J],Organometallics 2008,27(22):5744-5747.
[6]Esteruelas M A,Masamunt A B,Olivan M,Onate E,Valencia M,Aromatic Diosmatricyclic Nitrogen-Containing Compounds[J],J.Am.Chem.Soc.2008,130(35):11612-11613.
[7]Bleeke J R,New P R,Blanchard J M B,Haile t,Beatty A M,Synthesis of a New Family of Metallafurans from (Oxapentadienyl)metal Precursors[J],Organometallics 1995,14(11):5127-5137.
[8]DeShong P,Sidler D R,Rybczynski P J,Slough G A,Rheingold A L,A General Method for the Preparation of Carbonyl Compounds and Butenolides from Organomanganese Pentacarbonyl Complexes[J],J.Am.Chem.Soc.1988,110(8):2575-2585.
[9]Davidson J L,Green M,Nyathi J C,Scott C,Stone F G A,Welch A J,Woodward P,Reactions of acyl-and alkyl-(tricarbonyl)(η~5-cyclopentadienyl)-molybdenum and -tungsten complexes with but-2-yne;molecular structures of [Mo(CO)(Bu~tNC)(η~3-{O-C(O)-CMe-CMe-CMe})(η~5-C_5H_5)]and [MO-C(O)-C(Me) {C(Me)}_2C(Me)-C(CF_3)-O(CO)(η~5-C_5H_5)][J],J.Chem.Soc.,Chem.Commun.1976,(18):714-715.
[10]Booth B L,Hargreaves R G,Reactions between methyl-,acetyl-,and phenylpentacarbonylmanganese and acetylenes[J],J.Chem.Soc.(A) 1970,(2):308-314.
[11]Espuelas J,Esteruelas M A,Lahoz F J,Oro L A,Valero C,Reactivity of OsHa(CO)(PiPr_3)_2 toward Terminal Alkynes:Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)(η~2-H_2)(CO)(PiPr_3)_2 (R = Ph,SiMe_3)[J],Organometallics 1993,12(3):663-670.
[12]Werner H,Weinand R,Otto H,Aromaten(phosphan)metall-komplexe:Ⅺ.Funfgliedrige osmaheterocyclen durch alkin-insertion in eine Os-I oder Os-H-bindung[J], J. Organomet. Chem. 1986, 307(1): 49-59.
[13] Herrmann W A, Ziegler M L, Serhadll 0, Organometallic Chemistry of Reactive Organic Compounds. 41. Metal-Induced Carbyne/Carbene Coupling with Buchner's Diazo Compound[J], Organometallics 1983,2(8): 958-962.
[14] Komiya S, Ito T, Cowie M, Yamamoto A, Ibers J A, Carbon-Hydrogen Bond Activation by Transition Metal Complexes. Oxidative Addition of Alkyl Methacrylate to Ruthenium. The Structure of Hydrido(2-n-butoxycarbonylpropenyl-Cl,O) tris(triphenylphosphine)ruthenium(Ⅱ)[J], J. Am. Chem. Soc. 1976, 98(13):3874-3884.
[15] Sunley G J, Menanteau P d C, Adams H, Bailey N A, Maitlis P M,Cyclometallation of Unsaturated Carboxylic Acids by Pentamethylcyclopentadienyl-rhodium and -iridium Complexes. Crystal Structures of [(C_5Me5)Ir(CPh=CHCO-O)(Me_2SO)] and [(C_5Me_5)Ir(CPh=CHCO-OMe)I]~+[J], J.Chem. Soc, Dalton Trans. 1989, (12): 2415-2421.
[16] Castarlenas R, Esteruelas M A, Martin M, Oro L A, C-H activation of methyl vinyl ketone in Ir(acac)[η~2-CH_2=CHC(O)CH_3](PCy_3)[J], J. Organomet. Chem. 1998,564(1-2): 241-247.
[17] Dirnberger T, Werner H, A Series of Hydrido(vinyl)iridium(Ⅲ) Complexes That Are Thermodynamically More Stable than Their Olefin Iridium(Ⅰ) Isomers[J],Organometallics 2005,24(21): 5127-5139.
[18] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[19] Lowe C, Shklover V, Berke H, Tetracarbonyl(triphenylpropenetriyl)rheniurn. A Delocalized rhenacyclobutadiene[J], Organometallics 1991,10(9): 3396-3399.
[20] Padolik L L, Galluci J C, Wojcicki A, Fischer-Type Rhenacyclobutadiene Complexes: Synthesis, Structure, and Nucleophilic Addition/Substitution and Oxidation Reactions[J], J. Am. Chem. Soc. 1993,115(22): 9986-9996.
[21] Garrett K E, Sheridan J B, Pourreau D B, Feng W C, Geoffroy G L, Staley D L,Rheingold A L, Transient Generation of the Reactive Carbene Complex [Cp(CO)_2W=CH(Tol)]~+ and Its Reactions with Alkynes To Form Vinylcarbene, Allyl,Naphthol, Diene, and Metallafuran Complexes[J], J. Am. Chem. Soc. 1989, 111(22):8383-8391.
[22] Woodworm B E, Frohnapfel D S, White P S, Templeton J L, Formation of Derivative Carbyne Complexes from Tp'(CO)_2M = CCH_3 (M = Mo, W)[J],Organometallics 1998,17(9): 1655-1662.
[23] Grotjahn D B, Hoerter J M, Hubbard J L, Double C-H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(Ⅰ) Using Alkynes. Synthesis of 1,4-Dien-3-ones[J], J. Am. Chem. Soc. 2004, 126(29): 8866-8867.
[24] Bruce M I, Hall B C, Skelton B W, White A H, Zaitseva N N, Oligomerisation of alkynes at a pentamethylcyclopentadienylruthenium centre[J], J. Chem. Soc, Dalton Trans. 2000: 2279-2286.
[25] Lu G-L, Roper W R, Wright L J, Clark G R, A 2-iridathiophene from reaction between IrCl(CS)(PPh_3)_2 and Hg(CH=CHPh)_2[J], J. Organomet. Chem. 2005, 690(4):972-981.
[26] Bleeke J R, Ortwerth M F, Chiang M Y, Electrophilic Addition to an Iridathiacyclopentene Complex. Synthesis of the First Metallathiophene[J],Organometalllics 1993, 12(4): 985-987.
[27] Bleeke J R, Ortwerth M F, Rohde A M, Thiapentadienyl-Iridium-Phosphine Chemistry[J], Organometallics 1995, 14(6): 2813-2826.
[28] Weller K J, Filippov I, Briggs P M, Wigley D E, Pyridine Degradation Intermediates as Models for Hydrodenitrogenation Catalysis: Preparation and Properties of a Metallapyridine Complex[J], Organometallics 1998, 17(3): 322-329.
[29] Bleeke J R, Blanchard J M B, Synthesis and Reactivity of a Metallapyrylium[J],J. Am. Chem. Soc. 1997, 119(23): 5443-5444.
[30] Bleeke J R, Hinkle P V, Rath N P, Synthesis, Structure, Spectroscopy, and Reactivity of a Metallathiabenzene[J], J. Am. Chem. Soc. 1999, 121(3): 595-596.
[31] Bianchini C, Meli A, Peruzzini M, Vizza F, Frediani P, Herrera V,Sanchez-Delgado R A, Opening, Desulfurization, and Hydrogenation of Thiophene at Iridium. An Experimental Study in a Homogeneous Phase[J], J. Am. Chem. Soc. 1993, 115(7): 2731-2742.
[32] Chen J, Daniels L M, Angelici R J, New Modes of Thiophene Coordination and Reactivity: Structures of Cp~*Ir(η~2-thiophene), an Iridathiabenzene, and Cp~*Ir(η~4-thiophene·BH_3)[J], J. Am. Chem. Soc. 1990,112(1): 199-204.
[33] Clark G R, Johns P M, Roper W R, Wright L J, An Osmabenzofuran from Reaction between Os(PhC (?) CPh)(CS)(PPh_3)_2 and Methyl Propiolate and the C-Protonation of this Compound to Form a Tethered Osmabenzene[J],Organometallics 2006,25(7): 1771-1777.
[34] Bruce M I, Hall B C, Skelton B W, Tiekink E R T, White A H, Zaitseva N N,Some Pentamethylcyclopentadienyl-Ruthenium Derivatives of Methyl Propiolate[J],Aust. J. Chem. 2000, 53(2): 99-107.
[35] Grossmann U, Hund H-U, Bosch H W, Schmalle H, Berke H, Trimerisierung von Propiolsauremethylester an Dicarbonylbis (phosphordonor)eisen-Komplexen[J], J.Organomet. Chem. 1991, 408(2): 203-218.
[36] Birk R, Grossmann U, Hund H-U, Berke H, Koordination und Chemie von Acetylenen an dicarbonylbis (tirmethlphosphit)eisen-fragmenten[J], J. Organomet.Chem. 1988, 345(3): 321-329.
[37] Yamazaki H, Aoki K, A novel six-membered ruthenium metallocycle [J], J.Organomet. Chem. 1976, 122(3): C54-C58.
[38] Bianchini C, Meli A, Peruzzini M, Vizza F, Moneti S, Herrera V,S(?)nchez-Delgado R A, HDS Model Systems. Coordination, Opening, and Hydrogenation of Benzo[b] thiophene at Iridium[J], J. Am. Chem. Soc. 1994, 116(10):4370-4381.
[39] Wessig P, M(?)ller G, The Dehydro-Diels-Alder Reaction[J], Chem. Rev. 2008,108(6): 2051-2063.
[40] Brieger G, Bennett J N, The Intramolecular Diels-Alder Reaction[J], Chem. Rev.1980, 80(1): 63-97.
[41] Norton J A, The Diels-Alder Diene Synthesis[J], Chem. Rev. 1942, 31(2):319-523.
[42] Mellah M, Voituriez A, Schulz E, Chiral Sulfur Ligands for Asymmetric Catalysis[J],Chem.Rev.2007,107(11):5133-5209.
[43]Vogel P,Turks M,Bouchez L,Markovi(?) D,Varela-(?)lvarez A,Sordo J (?),New Organic Chemistry of Sulfur Dioxide[J],Acc.Chem.Res.2007,40(10):931-942.
[44]Yu N,Wang C,Zhao F,Liu L,Zhang W-X,Xi Z,Diverse Reactions of 1,4-Dilithio-1,3-dienes with Nitriles:Facile Access to Tricyclic △~1-Bipyrrolines,Multiply Substituted Pyridines,Siloles,and (Z,Z)- Dienylsilanes by Tuning of Substituents on the Butadienyl Skeleton[J],Chem.Eur.J.2008,14(18):5670-5679.
[45]Wang C,Wang C,Wang Q,Wang Z,Sun H,Guo X,Xi Z,Highly Efficient Synthesis of Stereodefined Multisubstituted 1,4-Dicyano- and 1-Cyano-1,3-butadienes and Their Reactions with Organolithium Reagents[J],Chem.Eur.J.2007,13(22):6484-6494.
[46]Wang C,Wang Z,Liu L,Wang C,Liu G,Xi Z,Cycloaddition Reactions of 1-Lithio-1,3-dienes with Aromatic Nitriles Affording Multiply Substituted Pyridines,Pyrroles,and Linear Butadienylimines[J],J.Org.Chem.2006,71(22):8565-8571.
[47]Chen J,Song Q,Wang C,Xi Z,Novel Cycloaddition of Nitriles with Monolithio- and Dilithiobutadienes[J],J.Am.Chem.Soc.2002,124(22):6238-6239.
[48]Hussain I,Yawer M A,Lalk M,Lindequist U,Villinger A,Fischer C,Langer P,Hetero-Diels-Alder reaction of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with arylsulfonylcyanides.Synthesis and antimicrobial activity of 4-hydroxy-2-(arylsulfonyl)pyridines[J],Bioorg.Med.Chem.2008,16(23):9898-9903.
[49]Emmrich T,Reinke H,Langer P,Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides[J],Synthesis 2006,(15):2551-2555.
[50]McClure C K,Link J S,2-Azabicyclo[2.2.2]octa-3,5-dione via a Nitrile Diels-Alder Reaction[J],J.Org.Chem.2003,68(21):8256-8257.
[51]Taylor E C,French L G,Intramolecular Diels-Alder Reactions of 1,2,4-Triazines.Routes to Condensed Pyrazines via Cycloaddition of Nitrile Dienophiles[J],J.Org.Chem.1989,54(6):1245-1249.
[52]Li W-T,Lai F-C,Lee G-H,Peng S-M,Liu R-S,Synthesis of Furopyridines via Cycloaddition of Unactivated Nitriles with Tungsten-Substituted l,3-Diene[J], J. Am.Chem. Soc. 1998,120(18): 4520-4521.
[53] Barluenga J, Fernandez-Rodriguez M (?), Garc(?)a-Garc(?)a P, Aguilar E,Gold-Catalyzed Intermolecular Hetero-Dehydro-Diels-Alder Cycloaddition of Captodative Dienynes with Nitriles: A New Reaction and Regioselective Direct Access to Pyridines[J], J. Am. Chem. Soc. 2008, 130(9): 2764-2765.
[54] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[55] Castarlenas R, Esteruelas M A, Onate E, Formation of Imine-Vinylidene-Osmium(Ⅱ) Derivatives by Hydrogen Transfer from Alkenyl Ligands to Azavinylidene Groups in Alkenyl-Azavinylidene-Osmium(Ⅳ) Complexes[J], Organometallics 2000, 19(25): 5454-5463.
[56] Castarlenas R, Esteruelas M A, Guti(?)-Puebla E, O(?)ate E, Reactivity of the Imine-Vinylidene Complexes OsCl-2(=C=CHPh)(NH-CR_2)(P~iPr_3)_2 [CR_2 = CMe_2,C(CH_2)-4CH_2][J], Organometallics 2001,20(8): 1545-1554.
[57] Zhu J, Jia G, Lin Z, Understanding Nonplanarity in Metallabenzene Complexes[J], Organometallics 2007,26(8): 1986-1995.
[58] Bolano T, Castarlenas R, Esteruelas M A, Onate E, Hydride-Carbyne to Carbene Transformation in an Osmium-Acetate-Bis(triisopropylphosphine) System: Influence of the Coordination Mode of the Carboxylate and the Reaction Solvent[J],Organometallics 2007,26(8): 2037-2041.
[59] Bolano T, Castarlenas R, Esteruelas M A, Modrego F J, Onate E,Hydride-Alkenylcarbyne to Alkenylcarbene Transformation in Bisphosphine-Osmium Complexes[J], J. Am. Chem. Soc. 2005, 127(31): 11184-11195.
[60] Doxsee K M, Farahi J B, Hope H, Synthesis and Formal [4 + 2] Cycloaddition Reactions of Vinylimido Complexes of Titanocene[J], J. Am. Chem. Soc. 1991,113(23): 8889-8898.
[61] Holland R L, Bunker K D, Chen C H, Dipasquale A G, Rheingold A L, Baldridge K K, O'Connor J M, Reactions of a Metallacyclobutene Complex with Alkenes[J], J. Am. Chem. Soc. 2008, 130(31): 10093-10095.
[62] Gong L, Lin Y, He G, Zhang H, Wang H, Wen T B, Xia H, Synthesis and Characterization of an Air-Stable p-Osmaphenol[J], Organometallics 2008, 27(3):309-311.
[63] Esteruelas M A, Garc(?)a-Yebra C, Oliv(?)n M, Onate E, Tajada M A, The Dihydride-Osmium(Ⅳ) Complex [OsH-2(κ~2-O_2CCH-3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[64] Werner H, Esteruelas M A, Otto H, Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr_3)-2 (M = Ru, Os) with Alkynes. The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)-2[J], Organometallics 1986, 5(11):2295-2299.
[65] Terrier F, Rat and Equilibrium Studies in Jackson-Meisenheimer Complexes[J],Chem. Rev. 1982, 82(2): 77-152.
[66] Paneque M, Posadas C M, Poveda M L, Rend(?)n N, Santos L L, Alvarez E,Salazar V, Mereiter K, O(?)ate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity[J], Organometallics 2007, 26(14): 3403-3415.
[67] a) Stephens P J, Devlin F J, Chabalowski C F, Frisch M J, Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields[J], J. Phys. Chem. 1994, 98(45): 11623-11627; b) Becke A D,Density-functional thermochemistry. III. The role of exact exchange[J], J. Chem. Phys.1993, 98(7): 5648-5652; c) Lee C, Yang W, Parr R G, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J],Phys. Rev. B. 1988, 37(2): 785-789.
[68] Couty M, Hall M B, Basis sets for transition metals: optimized outer p functions[J], J. Comput. Chem. 1996, 17(11):, 1359-1370.
[69] Check C E, Faust T O, Bailey J M, Wright B J, Gilbert T M, Sunderlin L S,Addition of Polarization and Diffuse Functions to the LANL2DZ Basis Set for P-Block Elements[J], J. Phys. Chem. A. 2001, 105(34): 8111-8116.
[70] Hay P J, Wadt W R, Ab initio Effective core potentials for molecular calculations. Potentials for potassium to gold including the outermost core orbitals[J], J. Chem.Phys. 1985, 82(1), 299-310.
[71] a) Petersson G A, Al-Laham M A, A complete basis set model chemistry. Ⅱ. Open-shell systems and the total energies of the first-row atoms[J], J. Chem. Phys.1991, 94(9): 6081-6090; b) Petersson G A, Bennett A, Tensfeldt T G, Al-Laham M A,Shirley W A, Mantzaris J, A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements[J], J. Chem. Phys. 1988,89(4): 2193-2218.
[72] a) Schleyer P v R, Maerker C, Dransfeld A, Jiao H, Hommes N J R v E,Nucleus-independent chemical shifts: a simple and efficient aromaticity probe[J], J.Am. Chem. Soc. 1996, 118(26): 6317-6318; b) Schleyer P v R, Jiao H, Hommes N J R v E, Malkin V G, Malkina O L, An Evaluation of the Aromaticity of Inorganic Rings: Refined Evidence from Magnetic Properties [J], J. Am. Chem. Soc. 1997,119(51): 12669-12670; c) Schleyer P v R, Manoharan M, Wang Z-X, Kiran B, Jiao H,Puchta R, Hommes N J R v E, Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity[J], Org Lett. 2001, 3(16): 2465-2468.
[73] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R,Montgomery J A, Vreven Jr, T, Kudin K N, Burant J C, Millam J M, Iyengar S S,Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A,Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P,Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O,Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A,Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C,Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q,Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P,Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A,Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A,Gaussian 03, Revision C. 02; Gaussian, Inc., Wallingford CT, 2004.
[2] Wright L J, Metallabenzenes and metallabenzenoids[J], Dalton Trans. 2006, (15):1821-1827.
[3] Landorf C W, Haley M M, Recent Advances in Metallabenzene Chemistry[J],Angew. Chem. Int. Ed. 2006,45(24): 3914-3936.
[4] Bleeke J R, Metallabenzenes [J], Chem. Rev. 2001, 101(5): 1205-1227.
[5] Jia G, Progress in the Chemistry of Metallabenzynes[J], Ace. Chem. Res. 2004,37(7): 479-486.
[6] Jia G, Recent progress in the chemistry of osmium carbyne and metallabenzyne complexes[J], Coord. Chem. Rev. 2007,251(17-20): 2167-2187.
[7] Weller K J, Filippov I, Briggs P M, Wigley D E, Pyridine Degradation Intermediates as Models for Hydrodenitrogenation Catalysis: Preparation and Properties of a Metallapyridine Complex[J], Organometallics 1998,17(3): 322-329.
[8] Bleeke J R, Blanchard J M B, Synthesis and Reactivity of a Metallapyrylium[J], J.Am. Chem. Soc. 1997, 119(23): 5443-5444.
[9] Bleeke J R, Hinkle P V, Rath N P, Synthesis, Structure, Spectroscopy, and Reactivity of a Metallathiabenzene[J], J. Am. Chem. Soc. 1999, 121(3): 595-596.
[10] Bianchini C, Meli A, Peruzzini M, Vizza F, Frediani P, Herrera V,Sanchez-Delgado R A, Opening, Desulfurization, and Hydrogenation of Thiophene at Iridium. An Experimental Study in a Homogeneous Phase[J], J. Am. Chem. Soc. 1993,115(7): 2731-2742.
[11] Chen J, Daniels L M, Angelici R J, New Modes of Thiophene Coordination and Reactivity: Structures of Cp~*Ir(η~2-thiophene), an Iridathiabenzene, and C~*Ir(η~4-thiophene·BH_3)[J], J.Am. Chem. Soc. 1990, 112(1): 199-204.
[12] Baya M, Esteruelas M A, Gonz(?)lez A I, L(?)pez A M, O(?)ate E, Formation of Azabutadienyl Fragments by Addition of the Isopropenyl Substituent of a Phosphine to Benzonitriles, Promoted by an Osmium Center[J], Organometallics 2005, 24(6):1225-1232.
[13]Bolano T,Castarlenas R,Esteruelas M A,Onate E,Assembly of an Allenylidene Ligand,a Terminal Alkyne,and an Acetonitrile Molecule:Formation of Osmacyclopentapyrrole Derivatives[J],J.Am.Chem.Soc.2006,128(12):3965-3973.
[14]Legzdins P,Lumb S A,Trapping of Cp*W(NO)(η~2-PhC≡CH),the KeyIntermediate in the C-H Activation of Alkanes byCp*W(NO)(CH_2SiMe_3)(CPh=CH_2)[J],Organometallics 1997,16(9):1825-1827.
[15]Alvarado Y,Daff P J,Perez P J,Poveda M L,Sanchez-Delgado R,Carmona E,Iridapyrrole Complexes via Formal 3 + 2 Cycloaddition of Iridium Alkenyls to Acetonitrile[J],Organometallics 1996,15(9):2192-2194.
[16]Bleeke J R,Putprasert P,Thananatthanachon T,Synthesis and Characterization of Fused-Ring Iridapyrroles[J],Organometallics 2008,27(22):5744-5747.
[17]Esteruelas M A,Masamunt A B,Olivan M,Onate E,Valencia M,Aromatic Diosmatricyclic Nitrogen-Containing Compounds[J],J.Am.Chem.Soc.2008,130(35):11612-11613.
[18]Bleeke J R,New P R,Blanchard J M B,Haile t,Beatty A M,Synthesis of a New Family of Metallafurans from (Oxapentadienyl)metal Precursors[J],Organometallics 1995,14(11):5127-5137.
[19]DeShong P,Sidler D R,Rybczynski P J,Slough G A,Rheingold A L,A General Method for the Preparation of Carbonyl Compounds and Butenolides from Organomanganese Pentacarbonyl Complexes[J],J.Am.Chem.Soc.1988,110(8):2575-2585.
[20]Davidson J L,Green M,Nyathi J C,Scott C,Stone F G A,Welch A J,Woodward P,Reactions of acyl-and alkyl-(tricarbonyl)(η~5-cyclopentadienyl)-molybdenum and -tungsten complexes with but-2-yne;molecular structures of [Mo(CO)(ButNC)(η~3- {O-C(O)-CMe-CMe-CMe})(η~5-C_5H_5)]and [MO-C(O)-C(Me){C(Me)}_2C(Me)-C(CF_3)-O(CO)(η~5-C_5H_5)][J],J.Chem.Soc.,Chem.Commun.1976,(18):714-715.
[21]Booth B L,Hargreaves R G,Reactions between methyl-,acetyl-,and phenylpentacarbonylmanganese and acetylenes[J],J.Chem.Soc.(A) 1970,(2):308-314.
[22] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4(CO)(PiPr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)(η~2-H_2)(CO)(P/Pr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993,12(3): 663-670.
[23] Werner H, Weinand R, Otto H, Aromaten(phosphan)metall-komplexe: XI. Funfgliedrige osmaheterocyclen durch alkin-insertion in eine Os-I oder Os-H-bindung[J], J. Organomet. Chem. 1986, 307(1): 49-59.
[24] Herrmann W A, Ziegler M L, Serhadll O, Organometallic Chemistry of Reactive Organic Compounds. 41. Metal-Induced Carbyne/Carbene Coupling with Buchner's Diazo Compound[J], Organometallics 1983,2(8): 958-962.
[25] Komiya S, Ito T, Cowie M, Yamamoto A, Ibers J A, Carbon-Hydrogen Bond Activation by Transition Metal Complexes. Oxidative Addition of Alkyl Methacrylate to Ruthenium. The Structure of Hydrido(2-n-butoxycarbonylpropenyl-C~1,O) tris(triphenylphosphine)ruthenium(Ⅱ)[J], J. Am. Chem. Soc. 1976, 98(13):3874-3884.
[26] Sunley G J, Menanteau P d C, Adams H, Bailey N A, Maitlis P M,Cyclometallation of Unsaturated Carboxylic Acids by Pentamethylcyclopentadienyl-rhodium and -iridium Complexes. Crystal Structures of [(C5Me5)Ir(CPh=CHCO-O)(Me2SO)] and [(C5Me5)Ir(CPh=CHCO-OMe)I]+[J], J.Chem. Soc, Dalton Trans. 1989, (12): 2415-2421.
[27] Castarlenas R, Esteruelas M A, Martin M, Oro L A, C-H activation of methyl vinyl ketone in Ir(acac)[η~2-CH_2=CHC(O)CH_3](PCy_3)[J], J. Organomet. Chem. 1998,564(1-2): 241-247.
[28] Dirnberger T, Werner H, A Series of Hydrido(vinyl)iridium(Ⅲ) Complexes That Are Thermodynamically More Stable than Their Olefin Iridium(Ⅰ) Isomers[J],Organometallics 2005, 24(21): 5127-5139.
[29] Li X, Chen P, Faller J W, Crabtree R H, Cycloiridation of a, P-Unsaturated Ketones, Esters, and Acetophenone[J], Organometallics 2005, 24(20): 4810-4815.
[30] Lowe C, Shklover V, Berke H, Tetracarbonyl(triphenylpropenetriyl)rhenium. A Delocalized rhenacyclobutadiene[J], Organometallics 1991,10(9): 3396-3399.
[31] Padolik L L, Galluci J C, Wojcicki A, Fischer-Type Rhenacyclobutadiene Complexes: Synthesis, Structure, and Nucleophilic Addition/Substitution and Oxidation Reactions [J], J. Am. Chem. Soc. 1993,115(22): 9986-9996.
[32] Garrett K E, Sheridan J B, Pourreau D B, Feng W C, Geoffroy G L, Staley D L,Rheingold A L, Transient Generation of the Reactive Carbene Complex [Cp(CO)_2W=CH(Tol)]~+ and Its Reactions with Alkynes To Form Vinylcarbene, Allyl,Naphthol, Diene, and Metallafuran Complexes[J], J. Am. Chem. Soc. 1989, 111(22):8383-8391.
[33] Woodworm B E, Frohnapfel D S, White P S, Templeton J L, Formation of Derivative Carbyne Complexes from Tp'(CO)_2M = CCH_3 (M = Mo, W)[J],Organometallics 1998,17(9): 1655-1662.
[34] Grotjahn D B, Hoerter J M, Hubbard J L, Double C-H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(I) Using Alkynes. Synthesis of l,4-Dien-3-ones[J], J. Am. Chem. Soc. 2004,126(29): 8866-8867.
[35] Bruce M I, Hall B C, Skelton B W, White A H, Zaitseva N N, Oligomerisation of alkynes at a pentamethylcyclopentadienylruthenium centre[J], J. Chem. Soc, Dalton Trans. 2000, (14): 2279-2286.
[36] Lu G-L, Roper W R, Wright L J, Clark G R, A 2-iridathiophene from reaction between IrCl(CS)(PPh_3)_2 and Hg(CH=CHPh)_2[J], J. Organomet. Chem. 2005, 690(4):972-981.
[37] Bleeke J R, Ortwerth M F, Chiang M Y, Electrophilic Addition to an Iridathiacyclopentene Complex. Synthesis of the First Metallathiophene[J],Organometalllics 1993,12(4): 985-987.
[38] Bleeke J R, Ortwerth M F, Rohde A M, Thiapentadienyl-Iridium-Phosphine Chemistry[J], Organometallics 1995,14(6): 2813-2826.
[39] Paneque M, Posadas C M, Poveda M L, Rendon N, Salazar V, Onate E, Mereiter K, Formation of Unusual Iridabenzene and Metallanaphthalene Containing Electron-Withdrawing Substituents[J], J. Am. Chem. Soc. 2003,125(33): 9898-9899.
[40] Paneque M, Posadas C M, Poveda M L, Rendon N, Santos L L, Alvarez E,Salazar V, Mereiter K, Onate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity[J], Organometallics 2007,26(14): 3403-3415.
[41] Zhang H, Feng L, Gong L, Wu L, He G, Wen T, Yang F, Xia H, Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC=CCH(OH)C=CH[J],Organometallics 2007,26(10): 2705-2713.
[42] Clark G R, Johns P M, Roper W R, Wright L J, An Osmabenzofuran from Reaction between Os(PhC = CPh)(CS)(PPh3)2 and Methyl Propiolate and the C-Protonation of this Compound to Form a Tethered Osmabenzene[J],Organometallics 2006,25(7): 1771-1777.
[43] Thorn D L, Hoffman R, Delocalization in metallocycles[J], Nouv. J. Chim. 1979,3(1): 39-45.
[44] Elliott G P, Roper W R, Waters J M, Metallacyclohexatrienes or 'metallabenzenes.' Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)(CO)(PPh_3)_2][J], J. Chem. Soc, Chem. Commun. 1982, (14):811-813.
[45] Iron M A, Lucassen A C B, Cohen H, Boom M E V d, Martin J M L, A Computational Foray into the Formation and Reactivity of Metallabenzenes [J], J. Am.Chem. Soc. 2004,126(37): 11699-11710.
[46] Alvarez E, Paneque M, Poveda M L, Rend(?)n N, Formation of Iridabenzenes by Coupling of Iridacyclopentadienes and Alkenes[J], Angew. Chem. Int. Ed. 2006,45(3):474-477.
[47] Chin C S, Lee H, New Iridacyclohexadienes and Iridabenzenes by [2+2+1] Cyclotrimerization of Alkynes and Facile Interconversion between Iridacyclohexadienes and Iridabenzenes [J], Chem. Eur. J. 2004, 10(18): 4518-4522.
[48] Chin C S, Lee H, Eum M-S, Iridabenzenes from Iridacyclopentadienes: Unusual C-C Bond Formation between Unsaturated Hydrocarbyl Ligands[J], Organometallics 2005, 24(20): 4849-4852.
[49] Bleeke J R, Peng W-J, Synthesis, Structure, and Spectroscopy of Iridacyclohexadiene Complexes[J], Organometallics 1987, 6(7): 1576-1578.
[50] Bleeke J R, Xie Y-F, Peng W-J, Chiang M, Metallabenzene: Synthesis, Structure,and Spectroscopy of a l-Irida-3,5-dimethylbenzene Complex[J], J. Am. Chem. Soc. 1989,111(11):4118-4120.
[51]Gilbertson R D,Weakley T J R,Haley M M,Direct Synthesis of an Iridabenzene from a Nucleophilic 3-Vinyl-l-cyclopropene[J],J.Am.Chem.Soc.1999,121(11):2597-2598.
[52]Gilbertson R D,Weakley T J R,Haley M M,Synthesis,Characterization,and Isomerization of an Iridabenzvalene[J],Chem.Eur.J.2000,6(3):437-441.
[53]Wu H-P,Lanza S,Weakley T J R,Haley M M,Metallabenzenes and Valence Isomers.3.Unexpected Rearrangement of Two Regioisomeric Iridabenzenes to an (η~5-Cyclopentadienyl)iridium(Ⅰ) Complex[J],Organometallics 2002,21(14):2824-2826.
[54]Gilbertson R D,Lau T L S,Lanza S,Wu H-P,Weakley T J R,Haley M M,Synthesis,Spectroscopy,and Structure of a Family of Iridabenzenes Generated by the Reaction of Vaska-Type Complexes with a Nucleophilic 3-Vinyl-1-cyclopropene[J],Organometallics 2003,22(16):3279-3289.
[55]Wu H-P,Weakley T J R,Haley M M,Regioselective Formation of β-Alkyl-α-phenyliridabenzenes via Unsymmetrical 3-Vinylcyclopropenes:Probing Steric and Electronic Influences by Varying the Alkyl Ring Substituent[J],Chem.Eur.J.2005,11(4):1191-1200.
[56]Jacob V,Weakley T J R,Haley M M,Metallabenzenes and Valence Isomers.Synthesis and Characterization of a Platinabenzene[J],Angew.Chem.Int.Ed.2002,41 (18):3470-3473.
[57]Landorf C W,Jacob V,Weakley T J R,Haley M M,Rational Synthesis of Platinabenzenes[J],Organometallics 2004,23(6):1174-1176.
[58]Xia H,He G,Zhang H,Wen T B,Sung H H Y,Williams I D,Jia G,Osmabenzenes from the Reactions of HC ≡ CCH(OH)C ≡CH with OsX_2(PPh_3)_3 (X =Cl,Br)[J],J.Am.Chem.Soc.2004,126(22):6862-6863.
[59]Zhang H,Wu L,Lin R,Zhao Q,He G,Yang F,Wen T B,Xia H,Synthesis,Characterization and Electrochemical Properties of Stable Osmabenzenes Containing PPh3 Substituents[J],Chem.Eur.J.2009,15(14):3546-3559.
[60]Zhang H,Xia H,He G,Wen T B,Gong L,Jia G,Synthesis and Characterization of Stable Ruthenabenzenes[J], Angew. Chem. Int. Ed. 2006,45(18): 2920-2923.
[61] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[62] Gong L, Chen Z, Lin Y, He X, Wen T B, Xu X, Xia H, Osmabenzenes from Osmacycles Containing an η~2-Coordinated Olefin[J], Chem. Eur. J. 2009, 15(25):6258-6266.
[63] Wen T B, Zhou Z Y, Jia G, Synthesis and Characterization of a Metallabenzyne[J],Angew. Chem. Int. Ed. 2001,40(10): 1951-1954.
[64] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[65] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006, 128(2): 13742-13752.
[66] Bierstedt A, Clark G R, Roper W R, Wright L J, A 2-iridafuran from reaction between a 1-iridaindene and methyl propiolate[J], J. Organomet. Chem. 2006,691(18): 3846-3852.
[67] Bruce M I, Hall B C, Skelton B W, Tiekink E R T, White A H, Zaitseva N N,Some Pentamethylcyclopentadienyl-Ruthenium Derivatives of Methyl Propiolate[J],Aust. J. Chem. 2000, 53(2): 99-107.
[68] Grossmann U, Hund H-U, Bosch H W, Schmalle H, Berke H, Trimerisierung von Propiols(?)uremethylester an Dicarbonylbis (phosphordonor)eisen-Komplexen[J], J.Organomet. Chem. 1991, 408(2): 203-218.
[69] Birk R, Grossmann U, Hund H-U, Berke H, Koordination und Chemie von Acetylenen an dicarbonylbis (tirmethlphosphit)eisen-fragmenten[J], J. Organomet.Chem. 1988, 345(3): 321-329.
[70] Yamazaki H, Aoki K, A novel six-membered ruthenium metallocycle [J], J. Organomet.Chem.1976,122(3):C54-C58.
[1]Xia H,He G,Zhang H,Wen T B,Sung H H Y,Williams I D,Jia G,Osmabenzenes from the Reactions of HC≡CCH(OH)C≡CH with OsX_2(PPh_3)_3 (X=Cl,Br)[J],J.Am.Chem.Soc.2004,126(22):6862-6863.
[2]Zhang H,Wu L,Lin R,Zhao Q,He G,Yang F,Wen T B,Xia H,Synthesis,Characterization and Electrochemical Properties of Stable Osmabenzenes Containing PPh3 Substituents[J],Chem.Eur.J.2009,15(14):3546-3559.
[3]Gong L,Lin Y,Wen T B,Zhang H,Zeng B,Xia H,Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J],Organometallics 2008,27(11):2584-2589.
[4]Gong L,Chen Z,Lin Y,He X,Wen T B,Xu X,Xia H,Osmabenzenes from Osmacycles Containing an η~2-Coordinated Olefin[J],Chem.Eur.J.2009,15(25):6258-6266.
[5]Zhang H,Xia H,He G,Wen T B,Gong L,Jia G,Synthesis and Characterization of Stable Ruthenabenzenes[J],Angew.Chem.Int.Ed.2006,45(18):2920-2923.
[6]Zhang H,Feng L,Gong L,Wu L,He G,Wen T,Yang F,Xia H,Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC≡CCH(OH)C≡CH[J],Organometallics 2007,26(10):2705-2713.
[7]Shilov A E,Shul'pin G B,Activation of C-H bonds by Metal Complexes[J],Chem.Rev.1997,97(8):2879-2932.
[8]Wemer H,Esteruelas M A,Otto H,Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr_3)_2 (M = Ru,Os) with Alkynes.The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)_2[J],Organometallics 1986,5(11):2295 -2299.
[9]Gong L,Lin Y,He G,Zhang H,Wang H,Wen T B,Xia H,Synthesis and Characterization of an Air-Stable p-Osmaphenol[J],Organometallics 2008,27(3):309-311.
[10]Esteruelas M A,Garc(?)a-Yebra C,Oliv(?)n M,O(?)ate E,Tajada M A,The Dihydride-Osmium(Ⅳ) Complex [OsH_2(κ~2-O_2CCH_3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[11] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4( CO) (P/Pr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)( η~2-H_2)(CO)(P/Pr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993,12(3): 663-670.
[12] Buil M L, Esteruelas M A, Garc(?)a-Yebra C, Gutierrez-Puebla E, Olivan M,Hydride-Hydroxyosmacyclopropene versus Hydride-Hydroxycarbyne and Cyclic Hydroxycarbene: Influence of the Substituents at the C(OH) Carbon Atom of the Carbon Donor Ligand[J], Organometallics 2000, 19(11): 2184-2193.
[13] Rickard C E F, Roper W R, Williamson A, Wright L J, Exchange of boryl ligand substituents in Os[B(OEt)_2]Cl(CO)(PPh_3)_2[J], J. Organomet. Chem. 2004, 689(9):1609-1616.
[14] Esteruelas M A, Lahoz F J, O(?)ate E, Oro L A, Zeier B, Reactions of OsHCl(CO)(PiPr_3)_2 with Alkynl-1-ols: Synthesis of (Vinylcarbene)osmium(Ⅱ) Complexes[J], Organometallics 1994, 13(5): 1662-1668.
[15] Hoffmann P R, Caulton K G, Solution structure and dynamics of five-coordinated d6 complexes[J], J. Am. Chem. Soc. 1975, 97(15): 4221-4228.
[1] Bleeke J R, Aromatic Iridacycles[J], Acc. Chem. Res. 2007,40(10): 1035-1047.
[2] Wright L J, Metallabenzenes and metallabenzenoids[J], Dalton Trans. 2006, (15):1821-1827.
[3] Landorf C W, Haley M M, Recent Advances in Metallabenzene Chemistry [J],Angew. Chem. Int. Ed. 2006,45(24): 3914-3936.
[4] Bleeke J R, Metallabenzenes [J], Chem. Rev. 2001,101(5): 1205-1227.
[5] Jia G, Recent progress in the chemistry of osmium carbyne and metallabenzyne complexes[J], Coord. Chem. Rev. 2007,251(17-20): 2167-2187.
[6] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006,128(2): 13742-13752.
[7] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[8] Jia G, Progress in the Chemistry of Metallabenzynes [J], Acc. Chem. Res. 2004,37(7): 479-486.
[9] Wen T B, Ng S M, Hung W Y, Zhou Z Y, Lo M F, Shek L-Y, Williams I D, Lin Z,Jia G, Protonation and Bromination of an Osmabenzyne: Reactions Leading to the Formation of New Metallabenzynes[J], J. Am. Chem. Soc. 2003, 125(4): 884-885.
[10] Wen T B, Zhou Z Y, Jia G, Synthesis and Characterization of a Metallabenzyne[J],Angew. Chem. Int. Ed. 2001,40(10): 1951-1954.
[11] Paneque M, Posadas C M, Poveda M L, Rendon N, Salazar V, O(?)ate E, Mereiter K, Formation of Unusual Iridabenzene and Metallanaphthalene Containing Electron-Withdrawing Substituents[J], J. Am. Chem. Soc. 2003, 125(33): 9898-9899.
[12] Paneque M, Posadas C M, Poveda M L, Rendon N, Santos L L, (?)lvarez E,Salazar V, Mereiter K, Onate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity [J], Organometallics 2007, 26(14): 3403-3415.
[13] He G, Zhu J, Hung W Y, Wen T B, Sung H H-Y, Williams I D, Lin Z, Jia G, A Metallanaphthalyne Complex from Zinc Reduction of a Vinylcarbyne Complex [J],Angew. Chem. Int. Ed. 2007,46(47): 9065-9068.
[14] Esteruelas M A, Garc(?)a-Yebra C, Oliv(?)n M, O(?)ate E, Tajada M A, The Dihydride-Osmium(IV) Complex [OsH_2 (η~2-O_2CCH_3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[15] Espuelas J, Esteruelas M A, Lahoz F J, Oro L A, Valero C, Reactivity of OsH_4( CO) (P/Pr_3)_2 toward Terminal Alkynes: Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)( κ~2-H_2)(CO)(PzPr_3)_2 (R = Ph, SiMe_3)[J],Organometallics 1993, 12(3): 663-670.
[16] Werner H, Esteruelas M A, Otto H, Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr-3)_2 (M = Ru, Os) with Alkynes. The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)_2[J], Organometallics 1986, 5(11):2295-2299.
[17] Gong L, Lin Y, He G, Zhang H, Wang H, Wen T B, Xia H, Synthesis and Characterization of an Air-Stable p-Osmaphenol[J], Organometallics 2008, 27(3):309-311.
[18] Therrien B, Vieille-Petit L, S(?)ss-Fink G, X-ray crystallographic study of two dinuclear triply-bridged p-cymene osmium complexes[J], J. Mol. Struct. 2005,738(1-3): 161-163.
[19] Wen T B, Zhou Z Y, Lo M F, Williams I D, Jia G, Vinylidene, Allenylidene, and Carbyne Complexes from the Reactions of [OsCl_2(PPh_3)-3] with HC=CC(OH)Ph-2[J],Organometallics 2003,22(25): 5217-5225.
[20] Kuhlman R, Streib W E, Caulton K G, Protonation of Chloride in Os(H)_2Cl_2(P~iPr_3)_2: Synthesis of [ (P~iPr_3)_2H-2Os(μ-Cl)_3OsH_2(P~iPr-3)_2]CF_3SO-3[J], Inorg.Chem. 1995, 34(7): 1788-1792.
[21] Fanwick P E, Fraser I F, Tetrick S M, Walton R A, Multiply Bonded Octahalodiosmate(Ⅲ) Anions. 4. Reactions with Nitrogen and Phosphorus Donor Ligands That Lead to Cleavage of the Os=Os Bond[J], Inorg. Chem. 1987, 26(2):3786-3791.
[22] Bolano T, Castarlenas R, Esteruelas M A, Onate E, Hydride-Carbyne to Carbene Transformation in an Osmium-Acetate-Bis(triisopropylphosphine) System: Influence of the Coordination Mode of the Carboxylate and the Reaction Solvent[J],Organometallics 2007,26(8): 2037-2041.
[23] Bolano T, Castarlenas R, Esteruelas M A, Modrego F J, Onate E,Hydride-Alkenylcarbyne to Alkenylcarbene Transformation in Bisphosphine-Osmium complexes[J], J. Am. Chem. Soc. 2005,127(31): 11184-11195.
[24] Caulton K G, Factors governing the equilibrium between metal alkyl, alkylidene and alkylidyne: MCX_2R, X-M=CXR and X_2M=CR[J], J. Organomet. Chem. 2001,617-618,56-64.
[25] Spivak G J, Coalter J N, Oliv(?)n M, Eisenstein O, Caulton K G, Osmium Converts Terminal Olefins to Carbynes: α-Hydroge Migration Redox Isomers with Reversed Stability for Ruthenium and for Osmium[J], Organometallics 1998, 17(6): 999-1001.
[26] Pilar Barrio M A E a, Preparation and Characterization of an Isometallabenzene with the Structure of a l,2,4-Cyclohexatriene[J], J. Am. Chem. Soc. 2004, 126(7):1946-1947.
[27] Esteruelas M A, Gonzalez A I, Lopez A M, Onate E, An Osmium-Carbene Complex with Fischer-Schrock Ambivalent Behavior[J], Organometallics 2003, 22(3): 414-425.
[28] Furstner A, Davies P W, Alkyne metathesis [J], Chem. Commun. 2005, 18(5719):2307-2320.
[29] Bunz U H F, How Are Alkynes Scrambled[J], Science 2005, 308: 216-217.
[30] Zhang H, Feng L, Gong L, Wu L, He G, Wen T, Yang F, Xia H, Synthesis and Characterization of Stable Ruthenabenzenes Starting from HC=CCH(OH)C=CH[J],Organometallics 2007, 26(10): 2705-2713.
[31] Rickard C E F, Roper W R, Woodgate S D, Wright L J, Electrophilic Aromatic Substitution Reactions of a Metallabenzene: Nitration and Halogenation of the Osmabenzene[Os[C(SMe)CHCHCHCH]I(CO)(PPh_3)_2][J], Angew. Chem. Int. Ed.2000, 39(4): 750-752.
[32] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[33] Hung W Y, Zhu J, Wen T B, Yu K P, Sung H H Y, Williams I D, Lin Z, Jia G,Osmabenzenes from the Reactions of a Dicationic Osmabenzyne Complex[J], J. Am.Chem. Soc. 2006, 128(42): 13742-13752.
[34] Xia H, He G, Zhang H, Wen T B, Sung H H Y, Williams I D, Jia G,Osmabenzenes from the Reactions of HC=CCH(OH)C=CH with OsX-2(PPh_3)_3 (X =Cl, Br)[J], J. Am. Chem. Soc. 2004, 126(22): 6862-6863.
[35] Rickard C E F, Roper W R, Woodgate S D, Wright L J, Reaction between the thiocarbonyl complex, Os(CS)(CO)(PPh_3)_3, and propyne: crystal structure of a new sulfur-substituted osmabenzene[J], J. Organomet. Chem. 2001, 623: 109-115.
[36] Elliott G P, Roper W R, Waters J M, Metallacyclohexatrienes or 'metallabenzenes.' Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)(CO)(PPh-3)_2][J], J. Chem. Soc, Chem. Commun. 1982, (14):811-813.
[37] Cruickshank D W J, X-ray results on aromatic hydrocarbons [J], Tetrahedron 1962, 17(3-4): 155-161.
[38] Edwards A J, Willis A C, Wenger E, Reactions of Benzyne-Nickel(O) Complexes with Thioalkynes: Preparation and Coordination of Polydentate Thioethers Containing a 2,3-Naphthylene Backbone[J], Organometallics 2002,21(8): 1654-1661.
[39] Mashima K, Komura N, Yamagata T, Tani K, Synthesis and Crystal Structure of a Cationic Trinuclear Ruthenium(Ⅱ) complex, [Ru_3(μ_2-Cl)_3(μ_3-Cl)_2 [1,2-bis (diphenylphosphino)benzene}_3]PF-6[J], Inorg. Chem. 1997, 36(13): 2908-2912.
[40] Yeomans B D, Humphrey D G, Heath G A, Halide-birdged arsine- and phosphine-capped diruthenium complexes, [(R_3As)_3Ru(μ-X)_3Ru(AsR_3)_3]~+ and [(R_3P)_3Ru(μ-X)_3Ru(PR_3)_3]~+ (X = Cl or Br), as precursors to confacial mixed-valence ruthenium 'blues': spectroelectrochemical studies spanning the binuclear oxidation states Ⅱ,Ⅱ,Ⅱ,Ⅲ and Ⅲ,Ⅲ[J], J. Chem. Soc, Dalton Trans. 1997, (22): 4153-4166.
[41] Buil M L, Esteruelas M A, Garc(?)a-Yebra C, Guti(?)rrez-Puebla E, Olivan M,Hydride-Hydroxyosmacyclopropene versus Hydride-Hydroxycarbyne and Cyclic Hydroxycarbene: Influence of the Substituents at the C(OH) Carbon Atom of the Carbon Donor Ligand[J], Organometallics 2000,19(11): 2184-2193.
[42] Buil M L, Esteruelas M A, Goni E, Olivan M, Onate E, Displacement of Phenyl and Styryl Ligands by Benzophenone Imine and 2-Vinylpyridine on Ruthenium and Osmium[J], Organometallics 2006,25(12): 3076-3083.
[43] Castro-Rodrigo R, Esteruelas M A, Lopez A M, O(?)ate E, Reactions of a Dihydrogen Complex with Terminal Alkynes: Formation of Osmium-Carbyne and -Carbene Derivatives with the Hydridotris(pyrazolyl)borate Ligand[J],Organometallics 2008,27(14): 3547-3555.
[44] Rickard C E F, Roper W R, Williamson A, Wright L J, Exchange of boryl ligand substituents in Os[B(OEt)_2]Cl(CO)(PPh_3)_2[J], J. Organomet. Chem. 2004, 689(9):1609-1616.
[45] a) Stephens P J, Devlin F J, Chabalowski C F, Frisch M J, Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields[J], J. Phys. Chem. 1994, 98(45): 11623-11627; b) Becke A D,Density-functional thermochemistry. Ⅲ. The role of exact exchange[J], J. Chem. Phys.1993, 98(7): 5648-5652; c) Lee C, Yang W, Parr R G, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J], Phys. Rev. B. 1988, 37(2): 785-789.
[46] Couty M, Hall M B, Basis sets for transition metals: optimized outer p functions[J], J. Comput. Chem. 1996, 17(11): 1359-1370.
[47] Check C E, Faust T O, Bailey J M, Wright B J, Gilbert T M, Sunderlin L S,Addition of Polarization and Diffuse Functions to the LANL2DZ Basis Set for P-Block Elements[J], J. Phys. Chem. A. 2001,105(34): 8111-8116.
[48] Hay P J, Wadt W R, Ab initio Effective core potentials for molecular calculations.Potentials for potassium to gold including the outermost core orbitals[J], J. Chem.Phys. 1985, 82(1), 299-310.
[49] a) Petersson G A, Al-Laham M A, A complete basis set model chemistry. Ⅱ.Open-shell systems and the total energies of the first-row atoms[J], J. Chem. Phys.1991, 94(9): 6081-6090; b) Petersson G A, Bennett A, Tensfeldt T G, Al-Laham M A,Shirley W A, Mantzaris J, A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements[J], J. Chem. Phys. 1988,89(4): 2193-2218.
[50] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R,Montgomery J A, Vreven Jr, T, Kudin K N, Burant J C, Millam J M, Iyengar S S,Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A,Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P,Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O,Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A,Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C,Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q,Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P,Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A,Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A,Gaussian 03, Revision C. 02; Gaussian, Inc., Wallingford CT, 2004.
[1]Baya M,Esteruelas M A,Gonz(?)lez A I,L(?)pez A M,O(?)ate E,Formation of Azabutadienyl Fragments by Addition of the Isopropenyl Substituent of a Phosphine to Benzonitriles,Promoted by an Osmium Center[J],Organometallics 2005,24(6):1225-1232.
[2]Bolano T,Castarlenas R,Esteruelas M A,Onate E,Assembly of an Allenylidene Ligand,a Terminal Alkyne,and an Acetonitrile Molecule:Formation of Osmacyclopentapyrrole Derivatives[J],J.Am.Chem.Soc.2006,128(12):3965-3973.
[3]Legzdins P,Lumb S A,Trapping of Cp*W(NO)(η~2-PhC≡CH),the Key Intermediate in the C-H Activation of Alkanes by Cp*W(NO) (CH_2SiMe_3) (CPh=CH_2)[J],Organometallics 1997,16(9):1825-1827.
[4]Alvarado Y,Daff P J,Perez P J,Poveda M L,Sanchez-Delgado R,Carmona E,Iridapyrrole Complexes via Formal 3 + 2 Cycloaddition of Iridium Alkenyls toAcetonitrile[J],Organometallics 1996,15(9):2192-2194.
[5]Bleeke J R,Putprasert P,Thananatthanachon T,Synthesis and Characterization of Fused-Ring Iridapyrroles[J],Organometallics 2008,27(22):5744-5747.
[6]Esteruelas M A,Masamunt A B,Olivan M,Onate E,Valencia M,Aromatic Diosmatricyclic Nitrogen-Containing Compounds[J],J.Am.Chem.Soc.2008,130(35):11612-11613.
[7]Bleeke J R,New P R,Blanchard J M B,Haile t,Beatty A M,Synthesis of a New Family of Metallafurans from (Oxapentadienyl)metal Precursors[J],Organometallics 1995,14(11):5127-5137.
[8]DeShong P,Sidler D R,Rybczynski P J,Slough G A,Rheingold A L,A General Method for the Preparation of Carbonyl Compounds and Butenolides from Organomanganese Pentacarbonyl Complexes[J],J.Am.Chem.Soc.1988,110(8):2575-2585.
[9]Davidson J L,Green M,Nyathi J C,Scott C,Stone F G A,Welch A J,Woodward P,Reactions of acyl-and alkyl-(tricarbonyl)(η~5-cyclopentadienyl)-molybdenum and -tungsten complexes with but-2-yne;molecular structures of [Mo(CO)(Bu~tNC)(η~3-{O-C(O)-CMe-CMe-CMe})(η~5-C_5H_5)]and [MO-C(O)-C(Me) {C(Me)}_2C(Me)-C(CF_3)-O(CO)(η~5-C_5H_5)][J],J.Chem.Soc.,Chem.Commun.1976,(18):714-715.
[10]Booth B L,Hargreaves R G,Reactions between methyl-,acetyl-,and phenylpentacarbonylmanganese and acetylenes[J],J.Chem.Soc.(A) 1970,(2):308-314.
[11]Espuelas J,Esteruelas M A,Lahoz F J,Oro L A,Valero C,Reactivity of OsHa(CO)(PiPr_3)_2 toward Terminal Alkynes:Synthesis and Reactions of the Alkynyl-Dihydrogen Complexes OsH(C_2R)(η~2-H_2)(CO)(PiPr_3)_2 (R = Ph,SiMe_3)[J],Organometallics 1993,12(3):663-670.
[12]Werner H,Weinand R,Otto H,Aromaten(phosphan)metall-komplexe:Ⅺ.Funfgliedrige osmaheterocyclen durch alkin-insertion in eine Os-I oder Os-H-bindung[J], J. Organomet. Chem. 1986, 307(1): 49-59.
[13] Herrmann W A, Ziegler M L, Serhadll 0, Organometallic Chemistry of Reactive Organic Compounds. 41. Metal-Induced Carbyne/Carbene Coupling with Buchner's Diazo Compound[J], Organometallics 1983,2(8): 958-962.
[14] Komiya S, Ito T, Cowie M, Yamamoto A, Ibers J A, Carbon-Hydrogen Bond Activation by Transition Metal Complexes. Oxidative Addition of Alkyl Methacrylate to Ruthenium. The Structure of Hydrido(2-n-butoxycarbonylpropenyl-Cl,O) tris(triphenylphosphine)ruthenium(Ⅱ)[J], J. Am. Chem. Soc. 1976, 98(13):3874-3884.
[15] Sunley G J, Menanteau P d C, Adams H, Bailey N A, Maitlis P M,Cyclometallation of Unsaturated Carboxylic Acids by Pentamethylcyclopentadienyl-rhodium and -iridium Complexes. Crystal Structures of [(C_5Me5)Ir(CPh=CHCO-O)(Me_2SO)] and [(C_5Me_5)Ir(CPh=CHCO-OMe)I]~+[J], J.Chem. Soc, Dalton Trans. 1989, (12): 2415-2421.
[16] Castarlenas R, Esteruelas M A, Martin M, Oro L A, C-H activation of methyl vinyl ketone in Ir(acac)[η~2-CH_2=CHC(O)CH_3](PCy_3)[J], J. Organomet. Chem. 1998,564(1-2): 241-247.
[17] Dirnberger T, Werner H, A Series of Hydrido(vinyl)iridium(Ⅲ) Complexes That Are Thermodynamically More Stable than Their Olefin Iridium(Ⅰ) Isomers[J],Organometallics 2005,24(21): 5127-5139.
[18] Wen T B, Hung W Y, Sung H H Y, Williams I D, Jia G, Syntheses of Metallabenzynes from an Allenylcarbene Complex[J], J. Am. Chem. Soc. 2005,127(9): 2856-2857.
[19] Lowe C, Shklover V, Berke H, Tetracarbonyl(triphenylpropenetriyl)rheniurn. A Delocalized rhenacyclobutadiene[J], Organometallics 1991,10(9): 3396-3399.
[20] Padolik L L, Galluci J C, Wojcicki A, Fischer-Type Rhenacyclobutadiene Complexes: Synthesis, Structure, and Nucleophilic Addition/Substitution and Oxidation Reactions[J], J. Am. Chem. Soc. 1993,115(22): 9986-9996.
[21] Garrett K E, Sheridan J B, Pourreau D B, Feng W C, Geoffroy G L, Staley D L,Rheingold A L, Transient Generation of the Reactive Carbene Complex [Cp(CO)_2W=CH(Tol)]~+ and Its Reactions with Alkynes To Form Vinylcarbene, Allyl,Naphthol, Diene, and Metallafuran Complexes[J], J. Am. Chem. Soc. 1989, 111(22):8383-8391.
[22] Woodworm B E, Frohnapfel D S, White P S, Templeton J L, Formation of Derivative Carbyne Complexes from Tp'(CO)_2M = CCH_3 (M = Mo, W)[J],Organometallics 1998,17(9): 1655-1662.
[23] Grotjahn D B, Hoerter J M, Hubbard J L, Double C-H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(Ⅰ) Using Alkynes. Synthesis of 1,4-Dien-3-ones[J], J. Am. Chem. Soc. 2004, 126(29): 8866-8867.
[24] Bruce M I, Hall B C, Skelton B W, White A H, Zaitseva N N, Oligomerisation of alkynes at a pentamethylcyclopentadienylruthenium centre[J], J. Chem. Soc, Dalton Trans. 2000: 2279-2286.
[25] Lu G-L, Roper W R, Wright L J, Clark G R, A 2-iridathiophene from reaction between IrCl(CS)(PPh_3)_2 and Hg(CH=CHPh)_2[J], J. Organomet. Chem. 2005, 690(4):972-981.
[26] Bleeke J R, Ortwerth M F, Chiang M Y, Electrophilic Addition to an Iridathiacyclopentene Complex. Synthesis of the First Metallathiophene[J],Organometalllics 1993, 12(4): 985-987.
[27] Bleeke J R, Ortwerth M F, Rohde A M, Thiapentadienyl-Iridium-Phosphine Chemistry[J], Organometallics 1995, 14(6): 2813-2826.
[28] Weller K J, Filippov I, Briggs P M, Wigley D E, Pyridine Degradation Intermediates as Models for Hydrodenitrogenation Catalysis: Preparation and Properties of a Metallapyridine Complex[J], Organometallics 1998, 17(3): 322-329.
[29] Bleeke J R, Blanchard J M B, Synthesis and Reactivity of a Metallapyrylium[J],J. Am. Chem. Soc. 1997, 119(23): 5443-5444.
[30] Bleeke J R, Hinkle P V, Rath N P, Synthesis, Structure, Spectroscopy, and Reactivity of a Metallathiabenzene[J], J. Am. Chem. Soc. 1999, 121(3): 595-596.
[31] Bianchini C, Meli A, Peruzzini M, Vizza F, Frediani P, Herrera V,Sanchez-Delgado R A, Opening, Desulfurization, and Hydrogenation of Thiophene at Iridium. An Experimental Study in a Homogeneous Phase[J], J. Am. Chem. Soc. 1993, 115(7): 2731-2742.
[32] Chen J, Daniels L M, Angelici R J, New Modes of Thiophene Coordination and Reactivity: Structures of Cp~*Ir(η~2-thiophene), an Iridathiabenzene, and Cp~*Ir(η~4-thiophene·BH_3)[J], J. Am. Chem. Soc. 1990,112(1): 199-204.
[33] Clark G R, Johns P M, Roper W R, Wright L J, An Osmabenzofuran from Reaction between Os(PhC (?) CPh)(CS)(PPh_3)_2 and Methyl Propiolate and the C-Protonation of this Compound to Form a Tethered Osmabenzene[J],Organometallics 2006,25(7): 1771-1777.
[34] Bruce M I, Hall B C, Skelton B W, Tiekink E R T, White A H, Zaitseva N N,Some Pentamethylcyclopentadienyl-Ruthenium Derivatives of Methyl Propiolate[J],Aust. J. Chem. 2000, 53(2): 99-107.
[35] Grossmann U, Hund H-U, Bosch H W, Schmalle H, Berke H, Trimerisierung von Propiolsauremethylester an Dicarbonylbis (phosphordonor)eisen-Komplexen[J], J.Organomet. Chem. 1991, 408(2): 203-218.
[36] Birk R, Grossmann U, Hund H-U, Berke H, Koordination und Chemie von Acetylenen an dicarbonylbis (tirmethlphosphit)eisen-fragmenten[J], J. Organomet.Chem. 1988, 345(3): 321-329.
[37] Yamazaki H, Aoki K, A novel six-membered ruthenium metallocycle [J], J.Organomet. Chem. 1976, 122(3): C54-C58.
[38] Bianchini C, Meli A, Peruzzini M, Vizza F, Moneti S, Herrera V,S(?)nchez-Delgado R A, HDS Model Systems. Coordination, Opening, and Hydrogenation of Benzo[b] thiophene at Iridium[J], J. Am. Chem. Soc. 1994, 116(10):4370-4381.
[39] Wessig P, M(?)ller G, The Dehydro-Diels-Alder Reaction[J], Chem. Rev. 2008,108(6): 2051-2063.
[40] Brieger G, Bennett J N, The Intramolecular Diels-Alder Reaction[J], Chem. Rev.1980, 80(1): 63-97.
[41] Norton J A, The Diels-Alder Diene Synthesis[J], Chem. Rev. 1942, 31(2):319-523.
[42] Mellah M, Voituriez A, Schulz E, Chiral Sulfur Ligands for Asymmetric Catalysis[J],Chem.Rev.2007,107(11):5133-5209.
[43]Vogel P,Turks M,Bouchez L,Markovi(?) D,Varela-(?)lvarez A,Sordo J (?),New Organic Chemistry of Sulfur Dioxide[J],Acc.Chem.Res.2007,40(10):931-942.
[44]Yu N,Wang C,Zhao F,Liu L,Zhang W-X,Xi Z,Diverse Reactions of 1,4-Dilithio-1,3-dienes with Nitriles:Facile Access to Tricyclic △~1-Bipyrrolines,Multiply Substituted Pyridines,Siloles,and (Z,Z)- Dienylsilanes by Tuning of Substituents on the Butadienyl Skeleton[J],Chem.Eur.J.2008,14(18):5670-5679.
[45]Wang C,Wang C,Wang Q,Wang Z,Sun H,Guo X,Xi Z,Highly Efficient Synthesis of Stereodefined Multisubstituted 1,4-Dicyano- and 1-Cyano-1,3-butadienes and Their Reactions with Organolithium Reagents[J],Chem.Eur.J.2007,13(22):6484-6494.
[46]Wang C,Wang Z,Liu L,Wang C,Liu G,Xi Z,Cycloaddition Reactions of 1-Lithio-1,3-dienes with Aromatic Nitriles Affording Multiply Substituted Pyridines,Pyrroles,and Linear Butadienylimines[J],J.Org.Chem.2006,71(22):8565-8571.
[47]Chen J,Song Q,Wang C,Xi Z,Novel Cycloaddition of Nitriles with Monolithio- and Dilithiobutadienes[J],J.Am.Chem.Soc.2002,124(22):6238-6239.
[48]Hussain I,Yawer M A,Lalk M,Lindequist U,Villinger A,Fischer C,Langer P,Hetero-Diels-Alder reaction of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with arylsulfonylcyanides.Synthesis and antimicrobial activity of 4-hydroxy-2-(arylsulfonyl)pyridines[J],Bioorg.Med.Chem.2008,16(23):9898-9903.
[49]Emmrich T,Reinke H,Langer P,Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides[J],Synthesis 2006,(15):2551-2555.
[50]McClure C K,Link J S,2-Azabicyclo[2.2.2]octa-3,5-dione via a Nitrile Diels-Alder Reaction[J],J.Org.Chem.2003,68(21):8256-8257.
[51]Taylor E C,French L G,Intramolecular Diels-Alder Reactions of 1,2,4-Triazines.Routes to Condensed Pyrazines via Cycloaddition of Nitrile Dienophiles[J],J.Org.Chem.1989,54(6):1245-1249.
[52]Li W-T,Lai F-C,Lee G-H,Peng S-M,Liu R-S,Synthesis of Furopyridines via Cycloaddition of Unactivated Nitriles with Tungsten-Substituted l,3-Diene[J], J. Am.Chem. Soc. 1998,120(18): 4520-4521.
[53] Barluenga J, Fernandez-Rodriguez M (?), Garc(?)a-Garc(?)a P, Aguilar E,Gold-Catalyzed Intermolecular Hetero-Dehydro-Diels-Alder Cycloaddition of Captodative Dienynes with Nitriles: A New Reaction and Regioselective Direct Access to Pyridines[J], J. Am. Chem. Soc. 2008, 130(9): 2764-2765.
[54] Gong L, Lin Y, Wen T B, Zhang H, Zeng B, Xia H, Formation of Four Conjugated Osmacyclic Species in a One-Pot Reaction[J], Organometallics 2008,27(11): 2584-2589.
[55] Castarlenas R, Esteruelas M A, Onate E, Formation of Imine-Vinylidene-Osmium(Ⅱ) Derivatives by Hydrogen Transfer from Alkenyl Ligands to Azavinylidene Groups in Alkenyl-Azavinylidene-Osmium(Ⅳ) Complexes[J], Organometallics 2000, 19(25): 5454-5463.
[56] Castarlenas R, Esteruelas M A, Guti(?)-Puebla E, O(?)ate E, Reactivity of the Imine-Vinylidene Complexes OsCl-2(=C=CHPh)(NH-CR_2)(P~iPr_3)_2 [CR_2 = CMe_2,C(CH_2)-4CH_2][J], Organometallics 2001,20(8): 1545-1554.
[57] Zhu J, Jia G, Lin Z, Understanding Nonplanarity in Metallabenzene Complexes[J], Organometallics 2007,26(8): 1986-1995.
[58] Bolano T, Castarlenas R, Esteruelas M A, Onate E, Hydride-Carbyne to Carbene Transformation in an Osmium-Acetate-Bis(triisopropylphosphine) System: Influence of the Coordination Mode of the Carboxylate and the Reaction Solvent[J],Organometallics 2007,26(8): 2037-2041.
[59] Bolano T, Castarlenas R, Esteruelas M A, Modrego F J, Onate E,Hydride-Alkenylcarbyne to Alkenylcarbene Transformation in Bisphosphine-Osmium Complexes[J], J. Am. Chem. Soc. 2005, 127(31): 11184-11195.
[60] Doxsee K M, Farahi J B, Hope H, Synthesis and Formal [4 + 2] Cycloaddition Reactions of Vinylimido Complexes of Titanocene[J], J. Am. Chem. Soc. 1991,113(23): 8889-8898.
[61] Holland R L, Bunker K D, Chen C H, Dipasquale A G, Rheingold A L, Baldridge K K, O'Connor J M, Reactions of a Metallacyclobutene Complex with Alkenes[J], J. Am. Chem. Soc. 2008, 130(31): 10093-10095.
[62] Gong L, Lin Y, He G, Zhang H, Wang H, Wen T B, Xia H, Synthesis and Characterization of an Air-Stable p-Osmaphenol[J], Organometallics 2008, 27(3):309-311.
[63] Esteruelas M A, Garc(?)a-Yebra C, Oliv(?)n M, Onate E, Tajada M A, The Dihydride-Osmium(Ⅳ) Complex [OsH-2(κ~2-O_2CCH-3)(H_2O)(P~iPr_3)_2]BF_4 as a Precursor for Carbon-Carbon Coupling Reactions[J], Organometallics 2000, 19(24):5098-5106.
[64] Werner H, Esteruelas M A, Otto H, Insertion Reactions of the 16-Electron Complexes MHCI(CO)(P-i-Pr_3)-2 (M = Ru, Os) with Alkynes. The X-ray Crystal Structure of Os((E)-CH=CHPh)CI(CO)(P-i-Pr_3)-2[J], Organometallics 1986, 5(11):2295-2299.
[65] Terrier F, Rat and Equilibrium Studies in Jackson-Meisenheimer Complexes[J],Chem. Rev. 1982, 82(2): 77-152.
[66] Paneque M, Posadas C M, Poveda M L, Rend(?)n N, Santos L L, Alvarez E,Salazar V, Mereiter K, O(?)ate E, Metallacycloheptatrienes of Iridium(Ⅲ): Synthesis and Reactivity[J], Organometallics 2007, 26(14): 3403-3415.
[67] a) Stephens P J, Devlin F J, Chabalowski C F, Frisch M J, Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields[J], J. Phys. Chem. 1994, 98(45): 11623-11627; b) Becke A D,Density-functional thermochemistry. III. The role of exact exchange[J], J. Chem. Phys.1993, 98(7): 5648-5652; c) Lee C, Yang W, Parr R G, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J],Phys. Rev. B. 1988, 37(2): 785-789.
[68] Couty M, Hall M B, Basis sets for transition metals: optimized outer p functions[J], J. Comput. Chem. 1996, 17(11):, 1359-1370.
[69] Check C E, Faust T O, Bailey J M, Wright B J, Gilbert T M, Sunderlin L S,Addition of Polarization and Diffuse Functions to the LANL2DZ Basis Set for P-Block Elements[J], J. Phys. Chem. A. 2001, 105(34): 8111-8116.
[70] Hay P J, Wadt W R, Ab initio Effective core potentials for molecular calculations. Potentials for potassium to gold including the outermost core orbitals[J], J. Chem.Phys. 1985, 82(1), 299-310.
[71] a) Petersson G A, Al-Laham M A, A complete basis set model chemistry. Ⅱ. Open-shell systems and the total energies of the first-row atoms[J], J. Chem. Phys.1991, 94(9): 6081-6090; b) Petersson G A, Bennett A, Tensfeldt T G, Al-Laham M A,Shirley W A, Mantzaris J, A complete basis set model chemistry. I. The total energies of closed-shell atoms and hydrides of the first-row elements[J], J. Chem. Phys. 1988,89(4): 2193-2218.
[72] a) Schleyer P v R, Maerker C, Dransfeld A, Jiao H, Hommes N J R v E,Nucleus-independent chemical shifts: a simple and efficient aromaticity probe[J], J.Am. Chem. Soc. 1996, 118(26): 6317-6318; b) Schleyer P v R, Jiao H, Hommes N J R v E, Malkin V G, Malkina O L, An Evaluation of the Aromaticity of Inorganic Rings: Refined Evidence from Magnetic Properties [J], J. Am. Chem. Soc. 1997,119(51): 12669-12670; c) Schleyer P v R, Manoharan M, Wang Z-X, Kiran B, Jiao H,Puchta R, Hommes N J R v E, Dissected Nucleus-Independent Chemical Shift Analysis of π-Aromaticity and Antiaromaticity[J], Org Lett. 2001, 3(16): 2465-2468.
[73] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R,Montgomery J A, Vreven Jr, T, Kudin K N, Burant J C, Millam J M, Iyengar S S,Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A,Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P,Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O,Austin A J, Cammi R, Pomelli C, Ochterski J W, Ayala P Y, Morokuma K, Voth G A,Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C,Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q,Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P,Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A,Challacombe M, Gill P M W, Johnson B, Chen W, Wong M W, Gonzalez C, Pople J A,Gaussian 03, Revision C. 02; Gaussian, Inc., Wallingford CT, 2004.