卤甲基芳烃和三卤甲基芳烃合成研究
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摘要
卤甲基芳烃和三卤甲基芳烃是一类重要的有机中间体,主要用来合成染料、农药、医药以及聚合物等。它们中尤以三氟甲基芳烃化合物更显重要,由于它们分子结构中含有氟原子,能明显改善其稳定性、脂溶性以及生物活性,广泛应用于生物医药及农药等领域,因此卤甲基芳烃及三卤甲基芳烃的合成研究具有实际意义。一般卤甲基芳烃可以采用烷基苯卤化或苄醇衍生物转化等方法制备;而三卤甲基芳烃可以采用芳烃的三卤甲基化反应或芳烃三卤甲基的卤交换反应等方法制备。这些制备方法中大多数方法条件苛刻、选择性差。此外,芳环上其它取代基还会对合成反应造成不良影响。为了克服这些障碍,本论文旨在探索关于卤甲基芳烃及三卤甲基芳烃合成的新方法,主要研究内容包括以下几方面:
(1)芳烃的氯甲基化反应研究。研制出一种新型芳烃氯甲基化反应催化体系,该催化体系由液体Lewis酸、硫酸和醋酸组成,其催化活性可通过改变催化剂各组分配比以及硫酸浓度进行调控,并已成功用于催化具有不同反应活性芳烃的单氯甲基化与双氯甲基化反应,和传统方法相比较,氯甲基化反应选择性明显改善,产率大幅度提高。该催化体系可重复使用,并且体系内含有一定量水分,可以避免反应过程中产生有毒的氯甲醚。采用这种新催化体系合成了一系列单氯甲基及双氯甲基芳烃化合物,其中有6种化合物为新化合物。
(2)三氯甲基芳烃合成研究。研究了以苯膦四氯为转化剂或采用苯膦二氯与五氯化磷相结合,将芳酸或芳酰氯转化为三氯甲基芳烃。对影响反应的因素进行了研究,发现连有推电子基的苯膦二氯有促进反应的作用,而连有吸电子基团则减缓反应的进行;反应底物(芳酸或芳酰氯)的结构效应则相反,即连有吸电子基的芳酸有利于反应,而连有推电子基团则减缓反应的进行。此外,发现反应中生成的苯膦酰二氯可作为催化剂重复使用,并对转化反应的条件进行了改进与优化,合成出9个三氯甲基芳烃,其中2个是未见文献报道的新化合物。详细研究了由芳酸转化为三氯甲基芳烃的反应机理,证实了芳酸与苯膦酰二氯/五氯化磷反应生成三氯甲基芳烃的机制。
(3)溴甲基芳烃合成研究。首次采用甲基芳烃与三溴化硼反应合成溴甲基芳烃,成功实现了甲基芳烃的非自由基溴化反应。采用该方法合成了系列溴甲基芳烃,发现当芳环上带有吸电子取代基时,反应产率较低;而带有推电子基团时,产率较高。此外,还发现溶剂化能力弱的溶剂对反应有利,而溶剂化能力较强的溶剂因能降低亲电试剂的反应活性,对反应不利。对于该反应历程,可能是两分子三溴化硼先发生作用,形成BBr_2~+阳离子和BBr_4~-阴离子,随后阳离子BBr_2~+进攻甲苯衍生物的甲基,形成一碳阳离子中间体,该中间体继续和阴离子BBr_4~-作用,形成苄溴衍生物产物和HBBr_2,并释放一分子BBr_3。
(4)三溴甲基芳烃合成研究。提出了一种以三氯甲基芳烃为原料合成三溴甲基芳烃的新方法,该方法是基于三氯甲基芳烃与三溴化硼在室温条件下发生的亲电氯-溴交换反应,具有条件温和、选择性及收率高等特点。研究发现芳环上取代基的位阻效应对三氯甲基芳烃的氯-溴交换反应有很大影响,和对位带有取代基的底物相比,邻位取代底物的反应产率大幅度降低。采用此方法合成了系列三溴甲基芳烃化合物,其中4,4′-二(三溴甲基)联苯、4-溴甲基-1-(三溴甲基)苯、2-氟-1-(三溴甲基)苯、2-溴-1-(三溴甲基)苯为新化合物。此外,对三氯甲基芳烃与三溴化硼间的氯-溴交换反应机理进行了研究,其可能反应历程是三溴化硼作为亲电试剂首先进攻三氯甲基芳烃上的氯,形成二氯甲基芳烃碳正离子与三溴一氯化硼负离子络合物,接着络合物上的溴发生分子内转移,形成一溴二氯甲基芳烃和二溴一氯化硼。二者继续反应形成新络合物,随之进行氯-溴交换反应,直到生成三溴甲基芳烃和三氯化硼。
(5)三氟甲基芳烃合成研究。发现了一种新的氟交换试剂HF-PhPF_4,该氟交换试剂可以在较温和条件下将三氯甲基芳烃转化为三氟甲基芳烃。并在此基础上探索出以芳酸为原料经“一锅法”合成三氟甲基芳烃的新工艺,在芳酸三氯甲基化反应后,无需分离、提纯,即可直接进行氯氟交换反应合成三氟甲基芳烃。研究了“一锅法”合成三氟甲基芳烃的可能反应历程,首先芳酸经五氯化磷转化为芳酰氯,同时苯膦二氯转化为苯膦四氯,酰氯和苯膦四氯反应生成三氯甲基化合物;通入氟化氢之后,反应体系中剩余的苯膦四氯转化为苯膦四氟,它与氟化氢结合,电离出H~+和PhPF_5~-,H~+进攻三氯甲基形成一碳阳离子,然后该碳阳离子在PhPF_5~-作用下,脱去一分子氯化氢并形成一氟二氯甲基芳烃,如此反复,最后生成三氟甲基芳烃。
Halomethylated and trihalomethylated aromatics are of major importance and have found a large number of uses from dyes and polymers to pharmaceuticals and agrochemicals. Among them, benzotrifluoride derivatives constitute a particular class with specific properties, such as polarity, thermal and metabolic stabilities as well as the high lipophilicity brought by the trifluoromethyl moiety that enhances their bioavailability. These molecules are very useful in the biochemical fields as well as in the material design and synthesis. Consequently, a sustained interest has been focused on the halomethylated and trihalomethylated aromatics preparation. Traditionally, the former compounds can be obtained through either a direct halogenation of the benzylic methyl, or a deoxybromination of benzylic alcohol. Methods for the preparation of latter aromatic compounds include trihalomethylation of aromatics as well as the halogen exchange reactions. However, most protocols often give poor selectivity and require either toxic reagents or harsh conditions typically involving high temperature and long reaction time. In addition, some substituents on the aromatic ring may have adverse effects on these preparations. In order to overcome these barriers, this thesis research is aimed at developing novel and effective synthesis strategies for these halomethylated and trihalomethylated aromatic compounds.
(1) Chloromethylation of aromatics. Popular approach for the chloromethylation of aromatics is Blanc reaction, which is normally performed in the presence of insoluble Lewis acid. The use of Lewis acids is important to activate formaldehyde. In the present study, a novel catalytic system consisting of soluble Lewis acid, sulfuric acid and acetic acid has been developed and employed for the Blanc reaction of aryl compounds in the presence of formaldehyde and hydrogen chloride. Regioselective mono- and di-chloromethylation of aryl compounds with different reactivities have been successfully performed with this catalytic system in good yields. It is found that catalyst activity can be optimized and catalyst selectivity can be manipulated by adjusted the catalytic system compositions as well as the concentration of sulfuric acid. In addition, such catalysts can be reused multiple times, thus saving costs and energy and reducing environmental impact from disposal of spent catalysts.
(2) Synthesis of trichloromethylated aromatic compounds. Trichloromethylation reaction of aromatic carboxylic acids or aroylchlorides has been accomplished by using tetrachlorophenylphosphine or dichlorophenylphosphine/phosphoric chloride as the transforming agent. The trichloromethylation reaction can be well controlled and the phenylphosphonic dichloride produced in the process can be reclaimed for reuse. A series of trichloromethylated aromatics including two new compounds, such as 3-trichloromethylbromobenzene and 2-trichloromethylmethbenzenetoluene, have been synthesized. The influences and the mechanism of the reaction have also been studied. It was found that the reaction was accelerated obviously with the electron-pushing groups attached to dichlorophenylphosphine and was decreased with the electron-withdrawing groups attached. On the other hand, the effects of substituents of the aromatic acids (or aroylchloride) on the reaction were opposed.
(3) Preparation of benzyl bromide derivatives. A facile method for the benzylic monobromination of toluene derivatives has been developed using boron tribromide as bromine source at ambient temperature. The best conditions for boron tribromide mediated benzylic bromination were defined using toluene as model substrate. It is found that increasing temperature resulted in decreasing in the yield of benzyl bromide, but slightly increased the yield of benzal bromide. Similarly, increasing the equivalence of boron tribromide caused an increase in the yield of benzal bromide. In addition, the solvent has shown a dramatic influence on the bromination yields. Increasing the solvating power of solvent decreased the benzyl bromide yield. Alkylbenzenes with electron-pushing group on the aromatic ring were found to convert into their corresponding benzyl bromides in high yields. Under identical conditions, deactivated toluene derivatives afforded lower quantities amount of benzyl bromides. This bromiantion approach seems to have an ionic transition state with a positive charge on methyl carbon and ionic stabilization from nearby BBr_4~- anion, which is quite different from the traditional radical ones and appears attractive. Furthermore, this procedure allows the easy isolation of products since the by-product of the reaction, dibromoborane, is hydrolyzed to boric acid and hydrogen bromide upon treatment with water during the work-up procedure.
(4) Preparation of tribromomethylarenes. A novel approach for the synthesis of tribromomethylarenes by halogen exchange of trichloromethyl or trifluoromethyl arenes with boron tribromide has reported. A series of tribromomethylarenes were prepared efficiently from trifluoro(chloro)methylarenes at room temperature with boron tribromide as the brominating reagent. It is found that the reaction was accelerated for the substrates with electron-pushing groups on the aromatic ring and decreased by the presence of electron-withdrawing groups. In addition, the reaction was inhibited greatly when the substrate had a substituted group at the ortho-position. A likely mechanism for this reaction is presented. Electrophilic attack of boron tribromide on the trichloromethylated aromatic ring gives an ionic complex which results in the displacement of one of the chlorides by bromine. The displacement reaction can then take place between the aromatic CBrCl_2 group and BBr_2Cl until benzotribromide derivatives are formed. The high yield of the conversion of benzotrichloride into benzotribromide can be explained by assuming that the equilibria are shifted toward the formation of benzotribromide due to an escape of BCl_3 gas from the reaction system.
(5) Preparation of trifluoromethylarenes. Electrophilic chloro-fluorine exchange reaction between trichloromethylarenes and HF was catalyzed By various catalysts such as phosphorus pentachloride, arsenic pentachloride, antimony pentachloride tetrachlorophenylphosphine, and tetrachloro(n-butylphosphine), respectively. It was found that tetrachlorophenylphosphine had the highest catalytic activity for this chloro-fluorine exchange reaction. However, the real catalyst was PhPF_4, which was formed in-situ through the reaction of tetrachlorophenylphosphine and HF, providing the fluorinating reagent, PhPF_4-HF. Based on these study, an efficient one-pot approach was developed and used to transform aromatic carboxylic acids to their corresponding trifluoromethylarenes. The synthesis strategy included the treatment of aromatic carboxylic acids with excess tetrachlorophenylphosphine to afford their corresponding trichloromethylarenes, followed by HF to complete the halogen exchange reaction. A plausible mechanism for this reaction was proposed.
(1)芳烃的氯甲基化反应研究。研制出一种新型芳烃氯甲基化反应催化体系,该催化体系由液体Lewis酸、硫酸和醋酸组成,其催化活性可通过改变催化剂各组分配比以及硫酸浓度进行调控,并已成功用于催化具有不同反应活性芳烃的单氯甲基化与双氯甲基化反应,和传统方法相比较,氯甲基化反应选择性明显改善,产率大幅度提高。该催化体系可重复使用,并且体系内含有一定量水分,可以避免反应过程中产生有毒的氯甲醚。采用这种新催化体系合成了一系列单氯甲基及双氯甲基芳烃化合物,其中有6种化合物为新化合物。
(2)三氯甲基芳烃合成研究。研究了以苯膦四氯为转化剂或采用苯膦二氯与五氯化磷相结合,将芳酸或芳酰氯转化为三氯甲基芳烃。对影响反应的因素进行了研究,发现连有推电子基的苯膦二氯有促进反应的作用,而连有吸电子基团则减缓反应的进行;反应底物(芳酸或芳酰氯)的结构效应则相反,即连有吸电子基的芳酸有利于反应,而连有推电子基团则减缓反应的进行。此外,发现反应中生成的苯膦酰二氯可作为催化剂重复使用,并对转化反应的条件进行了改进与优化,合成出9个三氯甲基芳烃,其中2个是未见文献报道的新化合物。详细研究了由芳酸转化为三氯甲基芳烃的反应机理,证实了芳酸与苯膦酰二氯/五氯化磷反应生成三氯甲基芳烃的机制。
(3)溴甲基芳烃合成研究。首次采用甲基芳烃与三溴化硼反应合成溴甲基芳烃,成功实现了甲基芳烃的非自由基溴化反应。采用该方法合成了系列溴甲基芳烃,发现当芳环上带有吸电子取代基时,反应产率较低;而带有推电子基团时,产率较高。此外,还发现溶剂化能力弱的溶剂对反应有利,而溶剂化能力较强的溶剂因能降低亲电试剂的反应活性,对反应不利。对于该反应历程,可能是两分子三溴化硼先发生作用,形成BBr_2~+阳离子和BBr_4~-阴离子,随后阳离子BBr_2~+进攻甲苯衍生物的甲基,形成一碳阳离子中间体,该中间体继续和阴离子BBr_4~-作用,形成苄溴衍生物产物和HBBr_2,并释放一分子BBr_3。
(4)三溴甲基芳烃合成研究。提出了一种以三氯甲基芳烃为原料合成三溴甲基芳烃的新方法,该方法是基于三氯甲基芳烃与三溴化硼在室温条件下发生的亲电氯-溴交换反应,具有条件温和、选择性及收率高等特点。研究发现芳环上取代基的位阻效应对三氯甲基芳烃的氯-溴交换反应有很大影响,和对位带有取代基的底物相比,邻位取代底物的反应产率大幅度降低。采用此方法合成了系列三溴甲基芳烃化合物,其中4,4′-二(三溴甲基)联苯、4-溴甲基-1-(三溴甲基)苯、2-氟-1-(三溴甲基)苯、2-溴-1-(三溴甲基)苯为新化合物。此外,对三氯甲基芳烃与三溴化硼间的氯-溴交换反应机理进行了研究,其可能反应历程是三溴化硼作为亲电试剂首先进攻三氯甲基芳烃上的氯,形成二氯甲基芳烃碳正离子与三溴一氯化硼负离子络合物,接着络合物上的溴发生分子内转移,形成一溴二氯甲基芳烃和二溴一氯化硼。二者继续反应形成新络合物,随之进行氯-溴交换反应,直到生成三溴甲基芳烃和三氯化硼。
(5)三氟甲基芳烃合成研究。发现了一种新的氟交换试剂HF-PhPF_4,该氟交换试剂可以在较温和条件下将三氯甲基芳烃转化为三氟甲基芳烃。并在此基础上探索出以芳酸为原料经“一锅法”合成三氟甲基芳烃的新工艺,在芳酸三氯甲基化反应后,无需分离、提纯,即可直接进行氯氟交换反应合成三氟甲基芳烃。研究了“一锅法”合成三氟甲基芳烃的可能反应历程,首先芳酸经五氯化磷转化为芳酰氯,同时苯膦二氯转化为苯膦四氯,酰氯和苯膦四氯反应生成三氯甲基化合物;通入氟化氢之后,反应体系中剩余的苯膦四氯转化为苯膦四氟,它与氟化氢结合,电离出H~+和PhPF_5~-,H~+进攻三氯甲基形成一碳阳离子,然后该碳阳离子在PhPF_5~-作用下,脱去一分子氯化氢并形成一氟二氯甲基芳烃,如此反复,最后生成三氟甲基芳烃。
Halomethylated and trihalomethylated aromatics are of major importance and have found a large number of uses from dyes and polymers to pharmaceuticals and agrochemicals. Among them, benzotrifluoride derivatives constitute a particular class with specific properties, such as polarity, thermal and metabolic stabilities as well as the high lipophilicity brought by the trifluoromethyl moiety that enhances their bioavailability. These molecules are very useful in the biochemical fields as well as in the material design and synthesis. Consequently, a sustained interest has been focused on the halomethylated and trihalomethylated aromatics preparation. Traditionally, the former compounds can be obtained through either a direct halogenation of the benzylic methyl, or a deoxybromination of benzylic alcohol. Methods for the preparation of latter aromatic compounds include trihalomethylation of aromatics as well as the halogen exchange reactions. However, most protocols often give poor selectivity and require either toxic reagents or harsh conditions typically involving high temperature and long reaction time. In addition, some substituents on the aromatic ring may have adverse effects on these preparations. In order to overcome these barriers, this thesis research is aimed at developing novel and effective synthesis strategies for these halomethylated and trihalomethylated aromatic compounds.
(1) Chloromethylation of aromatics. Popular approach for the chloromethylation of aromatics is Blanc reaction, which is normally performed in the presence of insoluble Lewis acid. The use of Lewis acids is important to activate formaldehyde. In the present study, a novel catalytic system consisting of soluble Lewis acid, sulfuric acid and acetic acid has been developed and employed for the Blanc reaction of aryl compounds in the presence of formaldehyde and hydrogen chloride. Regioselective mono- and di-chloromethylation of aryl compounds with different reactivities have been successfully performed with this catalytic system in good yields. It is found that catalyst activity can be optimized and catalyst selectivity can be manipulated by adjusted the catalytic system compositions as well as the concentration of sulfuric acid. In addition, such catalysts can be reused multiple times, thus saving costs and energy and reducing environmental impact from disposal of spent catalysts.
(2) Synthesis of trichloromethylated aromatic compounds. Trichloromethylation reaction of aromatic carboxylic acids or aroylchlorides has been accomplished by using tetrachlorophenylphosphine or dichlorophenylphosphine/phosphoric chloride as the transforming agent. The trichloromethylation reaction can be well controlled and the phenylphosphonic dichloride produced in the process can be reclaimed for reuse. A series of trichloromethylated aromatics including two new compounds, such as 3-trichloromethylbromobenzene and 2-trichloromethylmethbenzenetoluene, have been synthesized. The influences and the mechanism of the reaction have also been studied. It was found that the reaction was accelerated obviously with the electron-pushing groups attached to dichlorophenylphosphine and was decreased with the electron-withdrawing groups attached. On the other hand, the effects of substituents of the aromatic acids (or aroylchloride) on the reaction were opposed.
(3) Preparation of benzyl bromide derivatives. A facile method for the benzylic monobromination of toluene derivatives has been developed using boron tribromide as bromine source at ambient temperature. The best conditions for boron tribromide mediated benzylic bromination were defined using toluene as model substrate. It is found that increasing temperature resulted in decreasing in the yield of benzyl bromide, but slightly increased the yield of benzal bromide. Similarly, increasing the equivalence of boron tribromide caused an increase in the yield of benzal bromide. In addition, the solvent has shown a dramatic influence on the bromination yields. Increasing the solvating power of solvent decreased the benzyl bromide yield. Alkylbenzenes with electron-pushing group on the aromatic ring were found to convert into their corresponding benzyl bromides in high yields. Under identical conditions, deactivated toluene derivatives afforded lower quantities amount of benzyl bromides. This bromiantion approach seems to have an ionic transition state with a positive charge on methyl carbon and ionic stabilization from nearby BBr_4~- anion, which is quite different from the traditional radical ones and appears attractive. Furthermore, this procedure allows the easy isolation of products since the by-product of the reaction, dibromoborane, is hydrolyzed to boric acid and hydrogen bromide upon treatment with water during the work-up procedure.
(4) Preparation of tribromomethylarenes. A novel approach for the synthesis of tribromomethylarenes by halogen exchange of trichloromethyl or trifluoromethyl arenes with boron tribromide has reported. A series of tribromomethylarenes were prepared efficiently from trifluoro(chloro)methylarenes at room temperature with boron tribromide as the brominating reagent. It is found that the reaction was accelerated for the substrates with electron-pushing groups on the aromatic ring and decreased by the presence of electron-withdrawing groups. In addition, the reaction was inhibited greatly when the substrate had a substituted group at the ortho-position. A likely mechanism for this reaction is presented. Electrophilic attack of boron tribromide on the trichloromethylated aromatic ring gives an ionic complex which results in the displacement of one of the chlorides by bromine. The displacement reaction can then take place between the aromatic CBrCl_2 group and BBr_2Cl until benzotribromide derivatives are formed. The high yield of the conversion of benzotrichloride into benzotribromide can be explained by assuming that the equilibria are shifted toward the formation of benzotribromide due to an escape of BCl_3 gas from the reaction system.
(5) Preparation of trifluoromethylarenes. Electrophilic chloro-fluorine exchange reaction between trichloromethylarenes and HF was catalyzed By various catalysts such as phosphorus pentachloride, arsenic pentachloride, antimony pentachloride tetrachlorophenylphosphine, and tetrachloro(n-butylphosphine), respectively. It was found that tetrachlorophenylphosphine had the highest catalytic activity for this chloro-fluorine exchange reaction. However, the real catalyst was PhPF_4, which was formed in-situ through the reaction of tetrachlorophenylphosphine and HF, providing the fluorinating reagent, PhPF_4-HF. Based on these study, an efficient one-pot approach was developed and used to transform aromatic carboxylic acids to their corresponding trifluoromethylarenes. The synthesis strategy included the treatment of aromatic carboxylic acids with excess tetrachlorophenylphosphine to afford their corresponding trichloromethylarenes, followed by HF to complete the halogen exchange reaction. A plausible mechanism for this reaction was proposed.
引文
[1]Olah,G.;Tolgyesi,W.S.In Friedel Crafts and Related Reactions,vol.Ⅱ,Part 2,Olah,G.,Ed.;Interscience:New York,1963,pp 659-784.
[2]Taylor,L.D.;Simon,N.S.Carcinogenicity of bis(chloromethyl) ether and chloromethyl methyl ether,Journal of Physical Chemistry,1974,78,2696-2696.
[3]Pinell,R.P.;Khune,G.D.;Khatri,N.A.;Manatt,S.L.Concerning the chloromethylation of alkylbenzenes and polystyrenes by chloromethyl methyl ether,Tetrahedron Letters,1984,25,3511-3514.
[4]Ootsuks,H.;Takedya,H.Chloromethylation of thioflavin,JP 05117202,1993.
[5]Selb,J.;Gallot,Y.Graft copolymers:2.Specific instability of some poly(styrene-g-2-vinyl pyridines) obtained from chloromethylated polystyrene,Polymer,1979,20,1268-1272.
[6]Sparrow,J.T.An improved procedure for the chloromethylation of polystyrene-divinyl benzene,Tetrahedron Letters,1975,16,4637-4638.
[7]Yamabe,T.;Umezawa,K.;Yoshida,S.;Takai,N.Piezodialysis:styrene-butadiene copolymer membranes,Desalination,1974,15,127-134.
[8]Feinberg,R.S.;Merrifield,R.B.Zinc chloride-catalyzed chloromethylation of resins for solid phase peptide synthesis,Tetrahedron,1974,30,3209-3212.
[9]Svetlov,A.K.;Demenkova,T.N.;Khomutov,L.I.Effect of the structure of "crosslinked"copolymers of styrene on the kinetics of chloromethylation,Polymer Science U.S.S.R.,1969,11,688-693.
[10]Svetlov,A.K.;Yesipov,G.Z.;Demenkova,T.N.;Grigor'eva,Z.V.;Poplavskii,K.L.;Khomutov,L.I.Kinetics of chloromethylation of"crosslinked" styrene copolymers,Polymer Science U.S.S.R.,1969,11,3175-3180.
[11]Yesipov,G.Z.;Svetlov,A.K.;Grigor'eva,Z.V.Chloromethylation reactions of"graft" copolymers of styrene and divinylbenzene,Polymer Science U.S.S.R.,1968,10,1345-1351.
[12]Davankov,A.B.;Santo,I.;Lilo,P.M.,High-molecular derivatives of α-methylstyrene-Ⅱ.Chloromethylation of copolymers of α-methylstyrene and divinylbenzene,Polymer Science U.S.S.R.,1963,4,859-864.
[13]Tou,J.C.;Kallos,G.T.Possible formation of bis(chloromethyl)ether from the reactions of formaldehyde and chloride ion,Analytical Chemistry,1976,48,958-963.
[14]Dare,S.Process for the production of chloromethyi phenethyl bromide,US Patent 4967026,1990.
[15]Bianchi,T.A.Substituted styrenes,US Patent 3927117,1975.
[16]Naikl,H.A.;McGrail,P.T.;MacKenzie,P.D.;Parsons,I.W.On the chloromethylation of polyetherethersulphone/polyethersulphone copolymers.The use of triflic acid as catalyst,Polymer,1992,33,166-169.
[17]Corrieroa,G.;Madaiob,A.;Mayolc,L.;Picciallib,V.;Sica,D.Rotalin A and B,two novel diterpene metabolites from the encrusting mediterranean sponge,Tetrahedron,1989,45,277-288.
[18]Gl(a|¨)nzer,B.I.;Csuk,R.Reaction of pyranoid and furanoid aldonolactones with chloromethyltrimethylsilane derived reagents,Carbohydrate Research,1991,220,79-92.
[19]Moshchinskaya,N.K.;Rezmchenko,V.V.;Markov,N.M.;Olifer,V.S.;Shposbnikgv,S.Z.;Spodarik,B.Z.;Golovnenko,F.P.;Revenko,L.M.Method of preparing chloromethylaromatic hydrocarbons,SU 727010,1980.
[20]Petrova R.A.;Beresin B.R.;Potapova T.I.;Toropova E.A.Khim.& Khim.Tekhnol,1986,29,55-59.
[21]Barker,P.L.;Bahia,C.4-Chloromethylation of 1-methyl-2-pyrryl ketones,Tetrahedron,1990,46,2691-2694.
[22]Weber,H.;Bier,K.Kreislaufverfahren zur chlormethylierung vinylaromatischer polymere,DD 236740,1986.
[23]Irabien,S.A.;Stewart,R.;Wuchter,R.B.Process of preparing chloromethylated aromatic material,EP 0327255,1989.
[24]Jerabek,K.;Setinek,K.C.Catalyst consisting of palladium and polymer ion exchanger compounds as carrier and method of its making,CS 8804341,1990.
[25]Vesely,V.;Schwarz,F.Method of preparation of the akylbenzylchlorides,CS 215315,1984.
[26]Takeya,H.;Otsuka,H.Production process for 1,4-naphthalene-dicarboxylic acid or 1-hydromethyl-4-naphthoic acid,JP 05163198,1993.
[27]Selva,M.;Trotta,F.;Tundo,P.Improved selectivity in chloromethylation of alkylbenzenes in presence of quaternary ammonia salts,Synthesis,1991,11,1003-1004.
[28]申东升,林原斌.3,4-亚甲二氧基正丙基苯的氯甲基化反应,合成化学,1997,5,202-204.
[29]王明慧,吴坚平,杨立荣.相转移催化法合成2-氯-3-氯甲基-噻吩及噻吩唑,应用化学,2006,23,106-108.
[30]张赛丹,方岩雄.离子液体催化乙苯、邻二甲苯及苯甲醚的氯甲基化反应研究,广东工业大学硕士论文,2007.
[31]黄敬平,方岩雄.离子液体催化甲苯、对二甲苯及间二甲苯的氯甲基化反应研究,广东工业大学硕士论文.2007.
[32]黄敬平,方岩雄,邓运泉.咪唑型室温离子液体介质中甲苯氯甲基化反应的研究,精细化工,2007,24,1200-1203.
[33]孙致远,张成祥.2-溴-4,6-双(氯甲基)间二甲苯及其析生物的合成,化学试剂,1998,20,297-299.
[34]邱滔,陈海群.新型荧光增白剂4,4′-双(2-苯乙烯磺酸基)-联苯的研制,江苏石油化工学院学报,1998,10,1-2.
[35]季锡平,吴剑平等.4,4′-二(氯甲基)联苯的合成,淮海工学院学院,1998,17,46-48.
[36]陈华,刘文明.荧光增白剂4,4′-双(2-磺酸钠苯乙烯基)联苯的合成,化工矿物与加工,1998,27,6-7.
[37]李光才.4,4′-二(氯甲基)联苯的合成,化学世界,2000,41,259-261.
[1]MeCormaek,W.B.Preparation of para-nitrobenzotrichloride,US Patent 4454360,1984.
[2]吴秀珍.2,4-二氯三氯甲苯合成条件的研究,化学工程师,1995,5,18-19.
[3]Kooyman,E.C.;Farenhorst,E.The relative reactivities of polycyclic aromatics towards trichloromethyl radicals,Transactions of the Faraday Society,1953,49,58-66.
[4]Kroschwitz J.I.;Howe-Grant,M.Kirk-othmer Encyclopedia of Chemical Technology,4~(th) ed.,vol.6,New York:John Wiley & Sons Inc.,1993.
[5]殷金柱,李复生,魏东炜.新型光敏催化剂用于甲苯侧链氯化反应,天津大学学报,2004,37,651-654.
[6]Kajigaeshi,S.;Kakinami,T.;Moriwaki,M.Benzylic chlofination of alkylaromatic compounds,Tetrahedron Letters,1988,29,5783-5786.
[7]Sah,K.C.;Chondhury,D.A process for the selective chlorination of side chain in aromatic compounds,IN Patent 147428,1980.
[8]Carlo,R.;Giuseppe,C.;Vittorio,M.Procedure for the photochlorination of alkyl-aromatic compounds,US Patent 5514254,1996.
[9]Davis,R.A.Photochlorination process for methyl aromatic compounds,US Patent 4046656,1977.
[10]Chen,M.;Li,D.Combined method producing para-chlorobenzoic aldehyde,para-chlorobenzoie acid,CN Patent 1060650,1992.
[11]Leebrick,J.R.;Park,R.;Ramsden,H.E.Trichloromethylation of chlorosubstituted benzenes,US Patent 3297771,1967.
[12]Mckendry,L.H.;Ricks,M.J.;Rogers,R.B.Method for converting carboxylic acid groups to trichloromethyl groups,US Patent 4419514,1983.
[13]Chupp,J.P.;Neumann,T.E.A process for preparing substituted benzotrichloride compounds,US Patent 4098831,1985.
[14]Dorran,H.J.;Coveney,D.J.Process for preparing flunixin and intermediates thereof,US Patent 5965735,1999.
[15]Manley,P.W.;Bold,G.2-amino-nicotinamide derivatives and their use as VEGF-receptor tyrosine kinase inhibitors,US Patent 6624174,2003.
[16]Beller,M.;M(a|¨)gerlein,W.;Indolese,A.F.;Fischer,C.Efficient palladium-catalyzed alkoxycarbonylation of N-heteroaryl chlorides-A practical synthesis of building blocks for pharmaceuticals and herbicides,Synthesis,2001;1098-1109.
[17]Takahashi,J.Kinetic study on the conversion of pyridine and quinolinecarboxylic acids to the corresponding trichloromethyl compound,Journal of Heterocyclic Chemistry,1978,15,893-898.
[18]黄润秋,王惠林,周佳.有机中间体制备,北京化学工业出版社,北京,1997,p.174.
[19]韩刚毅.三种苯基膦酸酯化合物的合成,化学试剂,1990,12,42-44.
[20]http://www.sigmaaldrich.com/Area_of_Interest/Asia_Pacific_Rim/China_Mainland.html.
[1]Shimizu,I.Preparation of α-arylpropionates as pharmaceuticals or their intermediates,JP 63278746,1998.
[2]Xiao,Y.;Yu,W.L.;Chua,S.J.Diastereo and enantioselective total synthesis of stigmatellin A,Chemistry-European Journal,2000,6,1318-1321.
[3]Wenseleers,W.;Stellacci,F.;Meyer,F.T.Five orders of magnitude enhancement of two-photon absorption for dyes on silver nanoparticle fractal clusters,Journal of Physical Chemistry B,2002,106,6853-6863.
[4]Yo,J.;Yang,S.K.;Jeong,M.Y.Bis-1,4-(p-diarylaminostryl)-2,5-dicyanobenzene derivatives with large two-photon absorption cross-sections,Organic Letter,2003,5,645-648.
[5]Chambers,R.D.;James,S.R.In Comprehensive Organic Chemistry;Barton,D.H.R.;Ollis,W.D.,Eds.;Pergamon Press:Oxford,1979,Vol.1,p.493.
[6]Hudlicky,M.;Hudlicky,T.In Chemistry of Functional Groups,Patai,S.;Rappoport,Z.,Eds.;Wiley:New York,1983,p.1021.
[7]Vinod,T.K.;Hart,H.Synthesis of self-filled,vaulted,and intracavity funetionalized cappedophanes,Journal of Organic Chemistry,1991,56,5630-5640.
[8]Otsuka,H.;Araki,K.;Matsmoto,H.;Harada,T.;Skinkai,S.Synthesis and NMR spectroscopic studies of bridged and capped calix[6]arenes:High-yield syntheses of unimolecular caged compounds from calix[6]arene,Journal of Organic Chemistry,1995,60,4862-4867.
[9]Chessa,G.;Scrivanti,A.Synthesis of dendritic polypyridines with ethoxycarbonyl groups as surfacefunctionality,Journal of the Chemical Society,Perkin Transactions,1996,1,307-311.
[10]Das,D.P.;Parida,K.M.Liquid phase bromination of phenol,Over heteropoly acidimpregnated titanium phosphate,Journal of Molecular Catalysis A,2006,253,70-78.
[11]Snell,J.M.;Weissherger,A.Organic Synthesis;John Wiley:New York,1955;Collect.Vol.Ⅲ,p 788.
[12]Stephenson,E.F.M.Organic Synthesis;John Wiley:New York,1963;Collect.Vol.Ⅲ,p 984.
[13]Huyser,B.S.The photochemically induced reactions of bromotrichloromethane with alkyl aromatics,Journal of the American Chemical Society,1960,82,391-393.
[14]Heiba,E.A.;Anderson,L.C.X-Ray initiated reactions,I.The addition of bromotrichloromethane to alkenes,Journal of the American Chemical Society,1957,79,4940-4943.
[15]Huyser,E.S.The Photochemically induced reactions of bromotrichloromethane with alkyl aromatics,Journal of the American Chemical Society,1960,82,391-393.
[16]Hori,Y.;Nagano,Y.;Uchiyama,H.;Yamada,Y.;Taniguchi,H.Bromination of active hydrogen compounds by bromotrichloromethane and 1,8-diazabicyclo[5.4.0]undecene-7.A convenient synthesis for bromides and olefins,Chemistry Letters,1978,7,73-76.
[17]Bright,W.M.;Cammarata,P.Bromomethylation;Preparation of 2,6-bis-(bromomethyl)-4-alkyl phenols,Journal of the Chemical Society,1952,74,3690-3690.
[18]Sket,B.;Zupen,M.Polymers as reagents and catalysts.Part 12.Side chain bromination of aromatic molecules with a bromine complex of poly(styrene-co-4-vinylpyridine),Journal of Organic Chemistry,1986,51,929-931.
[19]Venkatachalapathy,C.;Pitchumani,K.Selectivity in bromination of alkylbenzenes in the presence of montmorillonite clay,Tetrahedran,1997,53,2581-2584.
[20]Clark,J.Green chemistry:challenges and opportunities,Green Chemistry,1999,1,1.
[21]Mestres,R.;Palenzuela,J.High atomic yield bromine-less benzylic bromination,Green Chemistry,2002,4,314-317.
[22]Kikuchi,D.;Sakaguchi,S.;Ishii,Y.An alternative method for the selective bromination of alkylbenzenes using NaBrO_3/NaHSO_3 reagent,Journal of Organic Chemistry,1998,63,6023-6026.
[23]Amati,A.;Dosualdo,G.;Zhao,L.H.;Bravo,A.;Fontana,F.;Minisci,F.;Bjorsvik,H.R.Catalytic processes,of oxidation by hydrogen peroxide in the presence of Br_2 or HBr.Mechanism and synthetic applications,Organic Process Research & Development,1998,2,261-269.
[24]李洪启,姚钟麒.1-溴-4-溴甲基苯的简易合成及应用,化学试剂,1996,18,364-365.
[25]Djerassi,C.Broaiinations with N-bromosuccinimide and related compounds,Chemical Review,1948,43,271-314.
[26]Wenner,W.Bis(bromomethyl) compounds,Journal of Organic Chemistry,1952,17,523-528.
[27]Wenner,W.Neuere methoden der pr(a|¨)parativen organischen chemie Ⅱ 14.N-bromsuccinimid,eigenschaften und reaktionsweisen studien zum ablauf der substitution,Angewandte Chemie,1959,71,349-365.
[28]Andrews,L.J.;Keefer,R.M.Benzylic bromination in the reactions of benzyl methyl ether and related compounds with N-bromosuccinimide.Journal of Organic Chemistry,1969,34,905-911.
[29]Lind,J.;Jonsson,M.;Xinhua,S.;Eriksen,T.E.;Eberson,L.Kinetics of radical-initiated chain bromination of 2-methyl-2-propanol by N-bromosuccinimide in water,Journal of the American Chemical Society,1993,115,3503-3510.
[30]Carreno,M.C.;Ruano,J.L.G.N-bromosuccinimide in acetonitrile:A mild and regiospecific nuclear brominating reagent for methoxybenzenes and naphthalenes,Journal of Organic Chemistry,1995,60,5328-5331.
[31]Dauben,H.J.Jr.;McCoy,L.L.N-bromosuccinimide I.Allylic bromination,a general survey of reaction variable,Journal of the American Chemical Society,1959,81,4863-4873.
[32]Walling,C.;Rieger,A.L.;Tanner,D.D.Positive halogen compounds Ⅷ.Structure and reactivity in N-bromosuccinimide brominations,Journal of the American Chemical Society,1963,85,3129-3134.
[33]Cram,D.J.;Helgeson,R.C.Macro rings ⅩⅩⅪⅤ.A ring expansion route to the higher paracyclophanes,and spectra-structure correlations of their derived ketones,Journal of the American Chemical Society,1966,88,3515-3521.
[34] Cochrane, W. P.; Pauson, P. L.; Stevens, T. S. Synthesis of symmetrically trisubstituted benzene derivatives, Journal of the Chemical Society, 1968,90,630-632.
[35] Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. Host-guest complexation 3. Organization of pyridyl binding sites, Journal of the American Chemical Society, 1977,99, 6392-6398.
[36] Iranpoor, N.; Firouzabadi, H.; Kazemi, F. Silicaphosphine (silphos): A filterable reagent for the conversion of alcohols and thiols to alkyl bromides and iodides, Tetrahedron, 2005,61, 5699-5704.
[37] Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F. Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions, Tetrahedron Letter, 2006,47,1771-1775.
[38] Iranpoor, N.; Firouzabadi, H.; Aghapour, G. A facile conversion of thiols to alkyl halides by triphenylphosphine/N-halosuceinimides, Synletter, 2001,7,1176-1178.
[39] Amijs, C. H. M; van Klink, G. P. M.; van Koten, G. Carbon tetrachloride free benzylic brominations of methyl aryl halides, Green Chemistry, 2003,5,470-474.
[40] Togo, H.; Hirai, T. Environmentally-friendly Wohlf-Ziegler bromination: Ionic-liquid reaction and solvent-free reaction, Synletter, 2003,702-704.
[41] Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Visible light induced 'on water' benzylic bromination with N-bromosuccinimide, Tetrahedron Letter, 2006,47,1097-1099.
[42] Shaw, H.; Perlmutter, H. D.; Gu, C; Arco, S. D.; Quibuyen, T. O. Free-radical bromination of selected organic compounds in water, Journal of Organic Chemistry, 1997, 62, 236-237.
[43] Rahman, A. N. M. M.; Bishop, R.; Tan, R.; Shan, N. Solid-state regio- and stereo-selective benzylic bromination of diquinoline compounds using N-bromosuccinimide, Green Chemistry, 2005, 7, 207-209.
[44] Kikuchi, D.; Sakaguchi, S.; Ishii, Y. An alternative method for the selective bromination of alkylbenzenes using NaBrO_3/NaHSO_3 regent, Journal of Organic Chemistry, 1998,63, 6023-6026.
[45] Amati, A.; Dosualdo, G.; Zhao, L. H.; Bravo, A.; Fontana, F.; Minisci, F.; Bjorsvik, H. R. Catalytic processes of oxidation by hydrogen peroxide in the presence of Br_2 or HBr. Mechanism and synthetic applications, Organic Process Research & Development, 1998,2, 261-269.
[46] Mestres, R.; Palenzuela, J. High atomic yield bromine-less benzylic bromination, Green Chemistry, 2002, 4, 314-316.
[47] Rothenberg, G.; Clark, J. H. On oxyhalogenation, acids, and non-mimics of bromoperoxidase enzymes, Green Chemistry, 2000,2,248-251.
[48] Sels, B.; De Vos, D.; Buntinx, M.; Pierard, F.; Kirsch-De Mesmaeker, A.; Jacobs, P. Layered double hydroxides exchanged with tungstate as biomimetic catalysts for mild oxidative bromination, Nature, 1999,400,855-857.
[49] Conte, V.; DiFuria, F.; Moro, S. Mimicking the vanadium bromoperoxidases reactions-mild and selective bromination of arenes and alkenes in a two-phase system, Tetrahedron Letter, 1996,37,8609-8612.
[50] Chaintreau, A.; Adrian, G.; Couturier, D. Cupric bromide as benzylic bromination reagent in polar media, Synthetic Communications, 1981,669-672.
[51] Amrollah-Madjdababi, A.; Pham, T. N.; Ashby, E. C. A simple method for the conversion of adamantyl, benzyl and benzyhydryl alcohols to their corresponding bromides and chlorides and the transhalogenation of adamantyl, benzyl, benzhydryl and tertiary alkyl bromides and chlorides, Synthesis, 1989,614-616.
[52] Brwon, H. C; Ramachandran, P. V. The boron approach to asymmetric synthesis, Pure Applied Chemistry, 1991, 63, 307.
[53] Brown, H. C; Ramachandran, P. V. Asymmetric reduction with chiral organoboranes based on alpha-pinene, Accounts of Chemical Research Search, 1992, 25, 16-24.
[54] Singh, V. K. Practical and useful methods for the enantioselective reduction of unsymmetrical ketones, Synthesis, 1992,605-617.
[55] Beardsley, D. A.; Fisher, G. B.; Goralski, C. T.; Nicolson, L. W.; Singaram, G. Boranes in synthesis 2. Asymmetric synthesis of p-amino alcohols. A facile conversion of 2-amino acetophenones to the corresponding p-amino alcohols in high enantiomeric purity, Tetrahedron Letter, 1994,35,1511 -1514.
[56] Barret, A. G. M.; Seefeld, M. A. A convenient asymmetric synthesis of anti-amino alcohols: an X-ray crystallographic study of (4R)-2,2-dimethyl-4-[(2S)-(diphenylmethyleneamino)-(lS)-hydroxy-3-buten-l-yl]-l,3-dioxolane., Journal of Chemical Society, Chemistry Communications, 1994,1053-1054.
[57] Kabalka, G. W.; Wu, Z.; Ju, Y. Reductive bromination of aromatic aldehydes using alkylboron dibromides, Tetrahedron Letter, 2000, 41, 5161-5164.
[58] Gruter, J. M.; Akkerman, O. S.; Bickelhaupt, F. Nuclear versus side-chain bromination of methyl-substituted anisoles by N-bromosuccinimide, Journal of Organic Chemistry, 1994, 59,4473-4481.
[1]Lutz,H.G.;Christian,B.Trisilylmethane as a structural backbone in multifunctional lithium amides:syntheses and structures of HC{(CH_3)_2SiN(Li)-tert-Bu}_3 and its solvate HC{(CH_3)_2SiN(Li)-tert-Bu}_3-2THF,Inorganic Chemistry,1993,32,2308-2314.
[2]Zhu,S.Z.Process for synthesizing alpha position perfluoro-p-xylene polymer,CN 1295996,2001.
[3]杜海堂,欧阳贵平,杜海军,史大斌,金林红.N-(取代)对三氟甲基苯基-1,3,5-三取代吡唑-4-酰胺衍生物的合成与生物活性,有机化学,2006,26,383-386.
[4]Sase,S.;Ogawa,N.;Fujioka,A.Fire-and heat-resistant polymaleimide compositions for electric circuit printed boards,JP 06136266,1994.
[5]杨芝萍,钟平,李术艳,汤日元.1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-氨基吡唑及其磺酰胺的合成及晶体结构,有机化学,2006,26,82-86.
[6]Jr.Doibier,W.R.;Duan,J.X.;Roche,A.A novel,non-high-dilution method for preparation of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane,Organic Letter,2000,2,1867-1869.
[7]William,T.G.;Pittsburgh,P.Method for promoting aluminum chloride catalyzed isomerization of sym-octahydrophenthrene to sym-octahydroanthracene with aralkyl halide,US 4385194,1982.
[8]Zhang,X.L.;Li,M.Reductive coupling reaction of trihalomethylarenes using the TiCl_4-Ga system,Chinese Journal of Organic Chemistry,1999,19,300-303.
[9]Mataka,S.;Liu,G.B.;Sawada,T.;Kurisu,M.;Tashiro,M.Photothermal side-chain bromination of methyl-,dimethyl-,and trimethylbenzenes with N-bromosuccinimide,Bulletin of the Chemical Society of Japan,1994,67,1113-1119.
[10]Mataka,S.;Kurisu,M.;Takahashi,K.;Tashiro,M.The bromination of methylarenes with NBS by irradiation using a tungsten lamp.Preparation of benzotribromides,Chemistry Letter,1984,11,1969-1972.
[11]Moushy,M.Trifluoromethyl substituted biphenyls and diphenyl ethers,Journal of the American Chemical Society,1952,74,1858-1859.
[12]Zhang,Y.H.;Shibatomi,K.;Yamamoto,H.Lewis acid-catalyzed highly selective halogenation of aromatic compounds,SynLetter,2005,2837-2842.
[13]Hunter,W.H.;Edger,D.E.Carbon tetrabromide as a brominating agent,Journal of the American Chemical Society,1932,54,2025-2028.
[14]Richard,H.M.;Marcus,E.H.;Paul,M.G.Regularities in the densities of dilute solutions of some monochlorobenzotrihalides,Journal of the American Chemical Society,1954,76,4737-4739.
[15]Heble,L.S.;Nadkarni,D.R.;Wheele,T.S.Mixed laterally-halogenated toluenes,Journal of Chemistry Society,1938,1322-1323.
[16]Mark,S.B.;Manjushrmi,M.A convenient transformation of benzyl bromides into (2-bromoethynyl)benzenes,Journal of the Chemical Society,Chemical Communications,1979,563-564.
[17]Mark,S.B.;Anthonyg,W.B.Reaction of allyl bromides with bromoform and base under phase transfer conditions,Journal of the Chemical Society,Chemical Communications,1979,210-211.
[18]Attilio,C.;Roberto,S.;Anselmo,P.Benzylic bromination-acetoxylation of toluenes by bromide ion-catalyzed thermal decomposition of peroxydisulfate in acetic acid in the presence of acetate ions,Journal of Organic Chemistry,1987,52,4925-4927.
[19]Yagupol'skii,L.M.;Kondratenko,N.V.Exchange of halogen atoms in trihalomethyl groups,Zhurnal Organicheskoi Khimii,1967,37,1770-1775.
[20]Castaiier,J.;Riera,J.;Carilla,J.;Robert,A.;Molins,E.;Miravitllest,C.A new trifluoromethylating agent:Synthesis of polychlorinated(trifluoromethyl)benzenes and 1,3-bis(trifluoromethyl)benzenes and conversion into their trichloromethyl counterparts and molecular structure of highly strained polychloro-m-xylenes,Journal of Organic Chemistry, 1991,56,103-110.
[21]Riera,J.;Castaiier,J.;Carilla,J.;Robert,A.New synthese of polychloro(trifluoromethyl)benzenes and highly strained polychloro(trichloromethyl)benzenes,Tetrahedron Letters,1989,30,3825-3828.
[22]Bloodworth,A.J.;Bowyer,K.J.A mild convenient halogen-exchange route to difluorides and trifluorides,Tetrahedron Letters,1987,28,5347-5350.
[23]Prakash,G.K.Surya;Hu,J.B.;Simon,J.;Bellew,D.R.;Olah,G.A.Preparation of α,α-difluoroalkanesulfonic acids,Journal of Fluorine Chemistry,2004,125,595-601.
[24]潘良金,朱旭容.相转移催化剂在对硝基三溴苄合成中的应用,江苏化工,2003,31,28-30.
[25]陈红飙,林原斌,罗和安,陈冠凡,刘展鹏,廖云峰.芳酸及其衍生物的三氯甲基化反应的研究,有机化学,2005,25,532-535.
[26]赵辉,陈红飙,刘展鹏,苏琼,林原斌.三溴甲基芳烃合成新方法的研究,有机化学,2007,27,1250-1253.
[1]黄维垣,杜灿屏,朱士正.中国有机氟化学十年进展,北京:高等教育出版社,1998,p201.
[2]王飞,刘小莉,胡满成.氟化学的发展及应用,陕西师范大学学报,2000,17,101-103.
[3]徐国耀.特殊的化学领域-有机氟化学,化工生产与技术,1994,3,1-6.
[4]Frosco,M.B.;Lawrence,L.E.;Barret,J.F.~(37)th interscience conference on antimicrobial agents and chemotherapy(ICAAC),Expert Opinion on Investigational Drugs,1997,6,1951-1968.
[5]Bryskier,A.Novelties in the field of fluoroqinolones,Expert Opinion on Investigational Drugs,1997,9,1227-1245.
[6]Wen,J.;Yin,H.;Tian,M.;Chen,Q.Synthesis and mesomorphic properties of 4-n-alkoxy4'-[4-((4-n-alkoxy-2,3,5,6-tetrafluorophenyl)ethynyl)benzyloxy]benzoates,Liquid Crystal,1995,19,511-517.
[7]Chen,B.;Yank,Y.;Wen,J.Synthesis and mesomorphic properties of 4-(1,1,7-trihydroperfluoroheptyloxycarbon-yl)phenyl-4'-n-alkoxybiphenyl-4-carboxylate,Liquid Crystal,1998,24,539-543.
[8]Ruppert,I.Nucleophilic trifluoromethylation with the reagent combination(Et_2N)_3P/CF_3Br,Journal of Fluorine Chemistry,1985,29,98-103.
[9]Wakselman,C.;Tordeux,M.Mild trifluoromethylation of organic compounds,Industrial Chemistry Library,1996,8,313-324.
[10]Kischkewitz,J.;Naumann,D.Comparison of the trifluoromethylating properties of(CF_3)_2Hg,CF_3I and(CF_3)_2Te:Reactions with olefinic and aromatic compounds,Journal of Fluorine Chemistry,1985,29,73-87.
[11]Sawada,H.;Nakayama,M.;Yoshida,M.;Yoshida,T.;Kamigata,N.Trifluoromethylation of aromatic compounds with bis(trifluoroacetyl) peroxide,Journal of Fluorine Chemistry,1990,46,423-431.
[12]Kobayashi,Y.;Kumadaki,I.Trifluoromethylation of aromatic compounds,Tetrahedron Letters,1969,10,4095-4096.
[13]Marhold,A.;Klauke,E.A new method for the tdfluoromethylation of aromatic compounds,Journal of Fluorine Chemistry,1980,16,516-520.
[14]Marhold,A.;Klauke,E.A new method for the trifluoromethylation of aromatics,Journal of Fluorine Chemistry,1981,18,281-291.
[15]Umemoto,T.;Ando,A.Synthesis and reactivity of N-trifluoromethyl-N-nitrosotrifluoromethanesulfonamide as a new type of trifluoromethylating agent,Bulletin of the Chemical Society of Japan,1986,59,447-452.
[16]Umemoto,T.Twenty years in my fluorine chemistry,Journal of Fluorine Chemistry,2000,105,211-213.
[17]Prakash,G K.S.;Krishnamurti,R.;Olah,G.A.Synthetic methods and reactions.141.Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane(TMS-CF_3).A trifluoromethide equivalent,Journal of the American Chemical Society,1989,111,393-395.
[18]Iseki,K.;Nagai,T.;Kobayashi,Y.Asymmetric trifluoromethylation of aldehydes and ketones with trifluoromethyltrimethylsilane catalyzed by chiralquaternary ammonium fluorides,Tetrahedron Letter,1994,35,3137-3138.
[19]Urata,H.;Fuchikami,T.A novel and convenient method for trifluoromethylation of organic halides using CF_3SiR'_3/KF/Cu(I) system,Tetrahedron Letters,1991,32,91-94.
[20]Kitazume,T.;Nakajima,S.Introduction of several trifluoromethyl groups onto the activated aromatic materials with CF_3TMS-CuI-KF system,Journal of Fluorine Chemistry,2004,125,1447-1449
[21]Hagiwara,T.;Mochizuki,H.;Fuchikami,T.Unique reactivity of aminoketones in the trifluoromethylation with trialkyl(trifluoromethyl)silanes,Synletter,1997,587-588.
[22]Matsui,K.;Tobita,E.;Ando,M.;Kondo,K.A convenient trifluoromethylation of aromatic halides with sodium trifluoroacetate,Chemistry Letters,1981,10,1719-1920.
[23]Yukihisa,N.;Takeshi,H.Japanese Patent 0413651,1990.
[24]Cart,G.E.;Chambers,R.D.;Holmes,T.F.;Parker,D.G.Sodium perfluoroalkane carboxylates as sources of perfluoroalkyl groups,Journal of the Chemical Society,Perkin Transactions,1988,1,921-926.
[25]Freskos,J.W.A convenient synthesis of pentafluoroethyl-substituted aromatics,Synthetic Communications,1988,18,965-972.
[26]Langlois,B.R.;Roques,N.Nucleophilic trifluoromethylation of aryl halides with methyl trifluoroacetate,Journal of Fluorine Chemistry,2007,128,1318-1325.
[27]Long,Z.;Duan,J.;Lin,Y.;Guo,C.;Chen,Q.Potassium 3-oxa-o-fluorosulfonyl perfluoropentanoate(FO_2SF_2CF_2CF_2OCF_2COOK),a low-temperature trifluoromethylating agent for organic halides;its a-carbon-oxygen bond fragmentation,Journal of Fluorine Chemistry,1996,78,177-181.
[28]Chen,Q.;Wu,S.Studies on fluoroalkylation and fluoroalkoxylation.Part 33.Direct trifluoromethylation of aryl halides with fluorosulphonyldifluoromethyl iodide in the presence of copper:an electron transfer induced process,Journal of the Chemical Society,Perkin Transactions,1989,1,2385-2387.
[29]Chen,Q.;Wu,S.Methyl fluorosulphonyldifluoroacetate;a new trifluoromethylating agent,Journal of the Chemical Society,Chemical Communications,1989,1,705.
[30]Chen,Q.;Yang,G.;Wu,S.Copper electron-transfer induced trifluoromethylation with methyl fluorosulphonyldifluoroacetate,Journal of Fluorine Chemistry,1991,55,291-298.
[31]Chen,Q.;Duan,J.Methyl 3-oxo-fluorosulfonylperfluoropentanoate:a versatile trifluoromethylating agent for organic halides,Journal of the Chemical Society,Chemical Communications,1993,1,1389-1342.
[32]Su,D.;Duan,J.;Chen,Q.Methyl chlorodifluoroacetate a convenient trifluoromethylating agent,Tetrahedron Letter,1991,32,7689-7690.
[33]McNeil,J.G.;Burton,D.J.Generation of trifluoromethylcopper from chlorodifluoroacetate, Journal of Fluorine Chemistry,1991,55,225-227.
[34]Duan,J.;Su,D.;Chen,Q.Trifluoromethylation of organic halides with methyl halodifluoroacetates-a process via difluorocarbene and trifluoromethide intermediates,Journal of Fluorine Chemistry,1993,61,279-284.
[35]Chen Q.;Duan,J.Copper induced single electron transfer trifluorbmethylation of organic halides with 3-oxo-ω-fluorosulfonylperfluoropentyl iodide,Chinese Journal of Chemistry,1994,12,464-470.
[36]Clark,J.H.;McClinton,M.A.;Jones,C.W.;Landon,P.;Bishop,D.;Blade,R.J.The effect of charcoal on the trifluoromethylation of aryl chlorides using Button's reagent,Tetrahedron Letters,1989,30,2133-2136.
[37]Howarth,M.S.;Seovell,E.G.;Watson,D.J.Process for the preparation of fluoromethylpyridines,US Patent 4745193,1986.
[38]Fung,A.P.;Wilson,C.A.Preparation of(trifluoromethyl)pyridines under liquid phase conditions,US Patent 4590279,1983.
[39]Fung,A.P.Liquid phase halogen exchange of(trichloromethyl) pyridines to (trifluoromethyl)pyridines,US Patent 4567273,1984.
[40]Erich,K.Fluorination of trichloromethyl groups,US Patent 4079089,1978.
[41]Murray,R.L.;Beanblossom,W.S.;Wojcik,B.H.Production of bis(Trifluoromethyl)benzene,Industrial and Engineering Chemistry,1947,39,302-305.
[42]Smith,W.C.Reaction of SF_4 with organic compounds containing a carbonyl radical,US Patent 2859245,1958.
[43]Ishida,M.;Koide,M.;Katsuhara,Y.Method for producing bis(trifluoromethyl)benzene,US Patent 6093858,2000.
[44]Marhold,A.;Kaethe,B.Method for producting trifluoromethylanilines,Japanese Patent 2001151736,2001.
[45]王秋玲.3,4-二氯三氟甲苯的合成方法,农药,1995,34,23-24.
[46]匡平.含氟芳香族化合物的合成及应用,辽宁化工,1992,12,47-52.
[2]Taylor,L.D.;Simon,N.S.Carcinogenicity of bis(chloromethyl) ether and chloromethyl methyl ether,Journal of Physical Chemistry,1974,78,2696-2696.
[3]Pinell,R.P.;Khune,G.D.;Khatri,N.A.;Manatt,S.L.Concerning the chloromethylation of alkylbenzenes and polystyrenes by chloromethyl methyl ether,Tetrahedron Letters,1984,25,3511-3514.
[4]Ootsuks,H.;Takedya,H.Chloromethylation of thioflavin,JP 05117202,1993.
[5]Selb,J.;Gallot,Y.Graft copolymers:2.Specific instability of some poly(styrene-g-2-vinyl pyridines) obtained from chloromethylated polystyrene,Polymer,1979,20,1268-1272.
[6]Sparrow,J.T.An improved procedure for the chloromethylation of polystyrene-divinyl benzene,Tetrahedron Letters,1975,16,4637-4638.
[7]Yamabe,T.;Umezawa,K.;Yoshida,S.;Takai,N.Piezodialysis:styrene-butadiene copolymer membranes,Desalination,1974,15,127-134.
[8]Feinberg,R.S.;Merrifield,R.B.Zinc chloride-catalyzed chloromethylation of resins for solid phase peptide synthesis,Tetrahedron,1974,30,3209-3212.
[9]Svetlov,A.K.;Demenkova,T.N.;Khomutov,L.I.Effect of the structure of "crosslinked"copolymers of styrene on the kinetics of chloromethylation,Polymer Science U.S.S.R.,1969,11,688-693.
[10]Svetlov,A.K.;Yesipov,G.Z.;Demenkova,T.N.;Grigor'eva,Z.V.;Poplavskii,K.L.;Khomutov,L.I.Kinetics of chloromethylation of"crosslinked" styrene copolymers,Polymer Science U.S.S.R.,1969,11,3175-3180.
[11]Yesipov,G.Z.;Svetlov,A.K.;Grigor'eva,Z.V.Chloromethylation reactions of"graft" copolymers of styrene and divinylbenzene,Polymer Science U.S.S.R.,1968,10,1345-1351.
[12]Davankov,A.B.;Santo,I.;Lilo,P.M.,High-molecular derivatives of α-methylstyrene-Ⅱ.Chloromethylation of copolymers of α-methylstyrene and divinylbenzene,Polymer Science U.S.S.R.,1963,4,859-864.
[13]Tou,J.C.;Kallos,G.T.Possible formation of bis(chloromethyl)ether from the reactions of formaldehyde and chloride ion,Analytical Chemistry,1976,48,958-963.
[14]Dare,S.Process for the production of chloromethyi phenethyl bromide,US Patent 4967026,1990.
[15]Bianchi,T.A.Substituted styrenes,US Patent 3927117,1975.
[16]Naikl,H.A.;McGrail,P.T.;MacKenzie,P.D.;Parsons,I.W.On the chloromethylation of polyetherethersulphone/polyethersulphone copolymers.The use of triflic acid as catalyst,Polymer,1992,33,166-169.
[17]Corrieroa,G.;Madaiob,A.;Mayolc,L.;Picciallib,V.;Sica,D.Rotalin A and B,two novel diterpene metabolites from the encrusting mediterranean sponge,Tetrahedron,1989,45,277-288.
[18]Gl(a|¨)nzer,B.I.;Csuk,R.Reaction of pyranoid and furanoid aldonolactones with chloromethyltrimethylsilane derived reagents,Carbohydrate Research,1991,220,79-92.
[19]Moshchinskaya,N.K.;Rezmchenko,V.V.;Markov,N.M.;Olifer,V.S.;Shposbnikgv,S.Z.;Spodarik,B.Z.;Golovnenko,F.P.;Revenko,L.M.Method of preparing chloromethylaromatic hydrocarbons,SU 727010,1980.
[20]Petrova R.A.;Beresin B.R.;Potapova T.I.;Toropova E.A.Khim.& Khim.Tekhnol,1986,29,55-59.
[21]Barker,P.L.;Bahia,C.4-Chloromethylation of 1-methyl-2-pyrryl ketones,Tetrahedron,1990,46,2691-2694.
[22]Weber,H.;Bier,K.Kreislaufverfahren zur chlormethylierung vinylaromatischer polymere,DD 236740,1986.
[23]Irabien,S.A.;Stewart,R.;Wuchter,R.B.Process of preparing chloromethylated aromatic material,EP 0327255,1989.
[24]Jerabek,K.;Setinek,K.C.Catalyst consisting of palladium and polymer ion exchanger compounds as carrier and method of its making,CS 8804341,1990.
[25]Vesely,V.;Schwarz,F.Method of preparation of the akylbenzylchlorides,CS 215315,1984.
[26]Takeya,H.;Otsuka,H.Production process for 1,4-naphthalene-dicarboxylic acid or 1-hydromethyl-4-naphthoic acid,JP 05163198,1993.
[27]Selva,M.;Trotta,F.;Tundo,P.Improved selectivity in chloromethylation of alkylbenzenes in presence of quaternary ammonia salts,Synthesis,1991,11,1003-1004.
[28]申东升,林原斌.3,4-亚甲二氧基正丙基苯的氯甲基化反应,合成化学,1997,5,202-204.
[29]王明慧,吴坚平,杨立荣.相转移催化法合成2-氯-3-氯甲基-噻吩及噻吩唑,应用化学,2006,23,106-108.
[30]张赛丹,方岩雄.离子液体催化乙苯、邻二甲苯及苯甲醚的氯甲基化反应研究,广东工业大学硕士论文,2007.
[31]黄敬平,方岩雄.离子液体催化甲苯、对二甲苯及间二甲苯的氯甲基化反应研究,广东工业大学硕士论文.2007.
[32]黄敬平,方岩雄,邓运泉.咪唑型室温离子液体介质中甲苯氯甲基化反应的研究,精细化工,2007,24,1200-1203.
[33]孙致远,张成祥.2-溴-4,6-双(氯甲基)间二甲苯及其析生物的合成,化学试剂,1998,20,297-299.
[34]邱滔,陈海群.新型荧光增白剂4,4′-双(2-苯乙烯磺酸基)-联苯的研制,江苏石油化工学院学报,1998,10,1-2.
[35]季锡平,吴剑平等.4,4′-二(氯甲基)联苯的合成,淮海工学院学院,1998,17,46-48.
[36]陈华,刘文明.荧光增白剂4,4′-双(2-磺酸钠苯乙烯基)联苯的合成,化工矿物与加工,1998,27,6-7.
[37]李光才.4,4′-二(氯甲基)联苯的合成,化学世界,2000,41,259-261.
[1]MeCormaek,W.B.Preparation of para-nitrobenzotrichloride,US Patent 4454360,1984.
[2]吴秀珍.2,4-二氯三氯甲苯合成条件的研究,化学工程师,1995,5,18-19.
[3]Kooyman,E.C.;Farenhorst,E.The relative reactivities of polycyclic aromatics towards trichloromethyl radicals,Transactions of the Faraday Society,1953,49,58-66.
[4]Kroschwitz J.I.;Howe-Grant,M.Kirk-othmer Encyclopedia of Chemical Technology,4~(th) ed.,vol.6,New York:John Wiley & Sons Inc.,1993.
[5]殷金柱,李复生,魏东炜.新型光敏催化剂用于甲苯侧链氯化反应,天津大学学报,2004,37,651-654.
[6]Kajigaeshi,S.;Kakinami,T.;Moriwaki,M.Benzylic chlofination of alkylaromatic compounds,Tetrahedron Letters,1988,29,5783-5786.
[7]Sah,K.C.;Chondhury,D.A process for the selective chlorination of side chain in aromatic compounds,IN Patent 147428,1980.
[8]Carlo,R.;Giuseppe,C.;Vittorio,M.Procedure for the photochlorination of alkyl-aromatic compounds,US Patent 5514254,1996.
[9]Davis,R.A.Photochlorination process for methyl aromatic compounds,US Patent 4046656,1977.
[10]Chen,M.;Li,D.Combined method producing para-chlorobenzoic aldehyde,para-chlorobenzoie acid,CN Patent 1060650,1992.
[11]Leebrick,J.R.;Park,R.;Ramsden,H.E.Trichloromethylation of chlorosubstituted benzenes,US Patent 3297771,1967.
[12]Mckendry,L.H.;Ricks,M.J.;Rogers,R.B.Method for converting carboxylic acid groups to trichloromethyl groups,US Patent 4419514,1983.
[13]Chupp,J.P.;Neumann,T.E.A process for preparing substituted benzotrichloride compounds,US Patent 4098831,1985.
[14]Dorran,H.J.;Coveney,D.J.Process for preparing flunixin and intermediates thereof,US Patent 5965735,1999.
[15]Manley,P.W.;Bold,G.2-amino-nicotinamide derivatives and their use as VEGF-receptor tyrosine kinase inhibitors,US Patent 6624174,2003.
[16]Beller,M.;M(a|¨)gerlein,W.;Indolese,A.F.;Fischer,C.Efficient palladium-catalyzed alkoxycarbonylation of N-heteroaryl chlorides-A practical synthesis of building blocks for pharmaceuticals and herbicides,Synthesis,2001;1098-1109.
[17]Takahashi,J.Kinetic study on the conversion of pyridine and quinolinecarboxylic acids to the corresponding trichloromethyl compound,Journal of Heterocyclic Chemistry,1978,15,893-898.
[18]黄润秋,王惠林,周佳.有机中间体制备,北京化学工业出版社,北京,1997,p.174.
[19]韩刚毅.三种苯基膦酸酯化合物的合成,化学试剂,1990,12,42-44.
[20]http://www.sigmaaldrich.com/Area_of_Interest/Asia_Pacific_Rim/China_Mainland.html.
[1]Shimizu,I.Preparation of α-arylpropionates as pharmaceuticals or their intermediates,JP 63278746,1998.
[2]Xiao,Y.;Yu,W.L.;Chua,S.J.Diastereo and enantioselective total synthesis of stigmatellin A,Chemistry-European Journal,2000,6,1318-1321.
[3]Wenseleers,W.;Stellacci,F.;Meyer,F.T.Five orders of magnitude enhancement of two-photon absorption for dyes on silver nanoparticle fractal clusters,Journal of Physical Chemistry B,2002,106,6853-6863.
[4]Yo,J.;Yang,S.K.;Jeong,M.Y.Bis-1,4-(p-diarylaminostryl)-2,5-dicyanobenzene derivatives with large two-photon absorption cross-sections,Organic Letter,2003,5,645-648.
[5]Chambers,R.D.;James,S.R.In Comprehensive Organic Chemistry;Barton,D.H.R.;Ollis,W.D.,Eds.;Pergamon Press:Oxford,1979,Vol.1,p.493.
[6]Hudlicky,M.;Hudlicky,T.In Chemistry of Functional Groups,Patai,S.;Rappoport,Z.,Eds.;Wiley:New York,1983,p.1021.
[7]Vinod,T.K.;Hart,H.Synthesis of self-filled,vaulted,and intracavity funetionalized cappedophanes,Journal of Organic Chemistry,1991,56,5630-5640.
[8]Otsuka,H.;Araki,K.;Matsmoto,H.;Harada,T.;Skinkai,S.Synthesis and NMR spectroscopic studies of bridged and capped calix[6]arenes:High-yield syntheses of unimolecular caged compounds from calix[6]arene,Journal of Organic Chemistry,1995,60,4862-4867.
[9]Chessa,G.;Scrivanti,A.Synthesis of dendritic polypyridines with ethoxycarbonyl groups as surfacefunctionality,Journal of the Chemical Society,Perkin Transactions,1996,1,307-311.
[10]Das,D.P.;Parida,K.M.Liquid phase bromination of phenol,Over heteropoly acidimpregnated titanium phosphate,Journal of Molecular Catalysis A,2006,253,70-78.
[11]Snell,J.M.;Weissherger,A.Organic Synthesis;John Wiley:New York,1955;Collect.Vol.Ⅲ,p 788.
[12]Stephenson,E.F.M.Organic Synthesis;John Wiley:New York,1963;Collect.Vol.Ⅲ,p 984.
[13]Huyser,B.S.The photochemically induced reactions of bromotrichloromethane with alkyl aromatics,Journal of the American Chemical Society,1960,82,391-393.
[14]Heiba,E.A.;Anderson,L.C.X-Ray initiated reactions,I.The addition of bromotrichloromethane to alkenes,Journal of the American Chemical Society,1957,79,4940-4943.
[15]Huyser,E.S.The Photochemically induced reactions of bromotrichloromethane with alkyl aromatics,Journal of the American Chemical Society,1960,82,391-393.
[16]Hori,Y.;Nagano,Y.;Uchiyama,H.;Yamada,Y.;Taniguchi,H.Bromination of active hydrogen compounds by bromotrichloromethane and 1,8-diazabicyclo[5.4.0]undecene-7.A convenient synthesis for bromides and olefins,Chemistry Letters,1978,7,73-76.
[17]Bright,W.M.;Cammarata,P.Bromomethylation;Preparation of 2,6-bis-(bromomethyl)-4-alkyl phenols,Journal of the Chemical Society,1952,74,3690-3690.
[18]Sket,B.;Zupen,M.Polymers as reagents and catalysts.Part 12.Side chain bromination of aromatic molecules with a bromine complex of poly(styrene-co-4-vinylpyridine),Journal of Organic Chemistry,1986,51,929-931.
[19]Venkatachalapathy,C.;Pitchumani,K.Selectivity in bromination of alkylbenzenes in the presence of montmorillonite clay,Tetrahedran,1997,53,2581-2584.
[20]Clark,J.Green chemistry:challenges and opportunities,Green Chemistry,1999,1,1.
[21]Mestres,R.;Palenzuela,J.High atomic yield bromine-less benzylic bromination,Green Chemistry,2002,4,314-317.
[22]Kikuchi,D.;Sakaguchi,S.;Ishii,Y.An alternative method for the selective bromination of alkylbenzenes using NaBrO_3/NaHSO_3 reagent,Journal of Organic Chemistry,1998,63,6023-6026.
[23]Amati,A.;Dosualdo,G.;Zhao,L.H.;Bravo,A.;Fontana,F.;Minisci,F.;Bjorsvik,H.R.Catalytic processes,of oxidation by hydrogen peroxide in the presence of Br_2 or HBr.Mechanism and synthetic applications,Organic Process Research & Development,1998,2,261-269.
[24]李洪启,姚钟麒.1-溴-4-溴甲基苯的简易合成及应用,化学试剂,1996,18,364-365.
[25]Djerassi,C.Broaiinations with N-bromosuccinimide and related compounds,Chemical Review,1948,43,271-314.
[26]Wenner,W.Bis(bromomethyl) compounds,Journal of Organic Chemistry,1952,17,523-528.
[27]Wenner,W.Neuere methoden der pr(a|¨)parativen organischen chemie Ⅱ 14.N-bromsuccinimid,eigenschaften und reaktionsweisen studien zum ablauf der substitution,Angewandte Chemie,1959,71,349-365.
[28]Andrews,L.J.;Keefer,R.M.Benzylic bromination in the reactions of benzyl methyl ether and related compounds with N-bromosuccinimide.Journal of Organic Chemistry,1969,34,905-911.
[29]Lind,J.;Jonsson,M.;Xinhua,S.;Eriksen,T.E.;Eberson,L.Kinetics of radical-initiated chain bromination of 2-methyl-2-propanol by N-bromosuccinimide in water,Journal of the American Chemical Society,1993,115,3503-3510.
[30]Carreno,M.C.;Ruano,J.L.G.N-bromosuccinimide in acetonitrile:A mild and regiospecific nuclear brominating reagent for methoxybenzenes and naphthalenes,Journal of Organic Chemistry,1995,60,5328-5331.
[31]Dauben,H.J.Jr.;McCoy,L.L.N-bromosuccinimide I.Allylic bromination,a general survey of reaction variable,Journal of the American Chemical Society,1959,81,4863-4873.
[32]Walling,C.;Rieger,A.L.;Tanner,D.D.Positive halogen compounds Ⅷ.Structure and reactivity in N-bromosuccinimide brominations,Journal of the American Chemical Society,1963,85,3129-3134.
[33]Cram,D.J.;Helgeson,R.C.Macro rings ⅩⅩⅪⅤ.A ring expansion route to the higher paracyclophanes,and spectra-structure correlations of their derived ketones,Journal of the American Chemical Society,1966,88,3515-3521.
[34] Cochrane, W. P.; Pauson, P. L.; Stevens, T. S. Synthesis of symmetrically trisubstituted benzene derivatives, Journal of the Chemical Society, 1968,90,630-632.
[35] Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. Host-guest complexation 3. Organization of pyridyl binding sites, Journal of the American Chemical Society, 1977,99, 6392-6398.
[36] Iranpoor, N.; Firouzabadi, H.; Kazemi, F. Silicaphosphine (silphos): A filterable reagent for the conversion of alcohols and thiols to alkyl bromides and iodides, Tetrahedron, 2005,61, 5699-5704.
[37] Firouzabadi, H.; Iranpoor, N.; Ebrahimzadeh, F. Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions, Tetrahedron Letter, 2006,47,1771-1775.
[38] Iranpoor, N.; Firouzabadi, H.; Aghapour, G. A facile conversion of thiols to alkyl halides by triphenylphosphine/N-halosuceinimides, Synletter, 2001,7,1176-1178.
[39] Amijs, C. H. M; van Klink, G. P. M.; van Koten, G. Carbon tetrachloride free benzylic brominations of methyl aryl halides, Green Chemistry, 2003,5,470-474.
[40] Togo, H.; Hirai, T. Environmentally-friendly Wohlf-Ziegler bromination: Ionic-liquid reaction and solvent-free reaction, Synletter, 2003,702-704.
[41] Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Visible light induced 'on water' benzylic bromination with N-bromosuccinimide, Tetrahedron Letter, 2006,47,1097-1099.
[42] Shaw, H.; Perlmutter, H. D.; Gu, C; Arco, S. D.; Quibuyen, T. O. Free-radical bromination of selected organic compounds in water, Journal of Organic Chemistry, 1997, 62, 236-237.
[43] Rahman, A. N. M. M.; Bishop, R.; Tan, R.; Shan, N. Solid-state regio- and stereo-selective benzylic bromination of diquinoline compounds using N-bromosuccinimide, Green Chemistry, 2005, 7, 207-209.
[44] Kikuchi, D.; Sakaguchi, S.; Ishii, Y. An alternative method for the selective bromination of alkylbenzenes using NaBrO_3/NaHSO_3 regent, Journal of Organic Chemistry, 1998,63, 6023-6026.
[45] Amati, A.; Dosualdo, G.; Zhao, L. H.; Bravo, A.; Fontana, F.; Minisci, F.; Bjorsvik, H. R. Catalytic processes of oxidation by hydrogen peroxide in the presence of Br_2 or HBr. Mechanism and synthetic applications, Organic Process Research & Development, 1998,2, 261-269.
[46] Mestres, R.; Palenzuela, J. High atomic yield bromine-less benzylic bromination, Green Chemistry, 2002, 4, 314-316.
[47] Rothenberg, G.; Clark, J. H. On oxyhalogenation, acids, and non-mimics of bromoperoxidase enzymes, Green Chemistry, 2000,2,248-251.
[48] Sels, B.; De Vos, D.; Buntinx, M.; Pierard, F.; Kirsch-De Mesmaeker, A.; Jacobs, P. Layered double hydroxides exchanged with tungstate as biomimetic catalysts for mild oxidative bromination, Nature, 1999,400,855-857.
[49] Conte, V.; DiFuria, F.; Moro, S. Mimicking the vanadium bromoperoxidases reactions-mild and selective bromination of arenes and alkenes in a two-phase system, Tetrahedron Letter, 1996,37,8609-8612.
[50] Chaintreau, A.; Adrian, G.; Couturier, D. Cupric bromide as benzylic bromination reagent in polar media, Synthetic Communications, 1981,669-672.
[51] Amrollah-Madjdababi, A.; Pham, T. N.; Ashby, E. C. A simple method for the conversion of adamantyl, benzyl and benzyhydryl alcohols to their corresponding bromides and chlorides and the transhalogenation of adamantyl, benzyl, benzhydryl and tertiary alkyl bromides and chlorides, Synthesis, 1989,614-616.
[52] Brwon, H. C; Ramachandran, P. V. The boron approach to asymmetric synthesis, Pure Applied Chemistry, 1991, 63, 307.
[53] Brown, H. C; Ramachandran, P. V. Asymmetric reduction with chiral organoboranes based on alpha-pinene, Accounts of Chemical Research Search, 1992, 25, 16-24.
[54] Singh, V. K. Practical and useful methods for the enantioselective reduction of unsymmetrical ketones, Synthesis, 1992,605-617.
[55] Beardsley, D. A.; Fisher, G. B.; Goralski, C. T.; Nicolson, L. W.; Singaram, G. Boranes in synthesis 2. Asymmetric synthesis of p-amino alcohols. A facile conversion of 2-amino acetophenones to the corresponding p-amino alcohols in high enantiomeric purity, Tetrahedron Letter, 1994,35,1511 -1514.
[56] Barret, A. G. M.; Seefeld, M. A. A convenient asymmetric synthesis of anti-amino alcohols: an X-ray crystallographic study of (4R)-2,2-dimethyl-4-[(2S)-(diphenylmethyleneamino)-(lS)-hydroxy-3-buten-l-yl]-l,3-dioxolane., Journal of Chemical Society, Chemistry Communications, 1994,1053-1054.
[57] Kabalka, G. W.; Wu, Z.; Ju, Y. Reductive bromination of aromatic aldehydes using alkylboron dibromides, Tetrahedron Letter, 2000, 41, 5161-5164.
[58] Gruter, J. M.; Akkerman, O. S.; Bickelhaupt, F. Nuclear versus side-chain bromination of methyl-substituted anisoles by N-bromosuccinimide, Journal of Organic Chemistry, 1994, 59,4473-4481.
[1]Lutz,H.G.;Christian,B.Trisilylmethane as a structural backbone in multifunctional lithium amides:syntheses and structures of HC{(CH_3)_2SiN(Li)-tert-Bu}_3 and its solvate HC{(CH_3)_2SiN(Li)-tert-Bu}_3-2THF,Inorganic Chemistry,1993,32,2308-2314.
[2]Zhu,S.Z.Process for synthesizing alpha position perfluoro-p-xylene polymer,CN 1295996,2001.
[3]杜海堂,欧阳贵平,杜海军,史大斌,金林红.N-(取代)对三氟甲基苯基-1,3,5-三取代吡唑-4-酰胺衍生物的合成与生物活性,有机化学,2006,26,383-386.
[4]Sase,S.;Ogawa,N.;Fujioka,A.Fire-and heat-resistant polymaleimide compositions for electric circuit printed boards,JP 06136266,1994.
[5]杨芝萍,钟平,李术艳,汤日元.1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-氨基吡唑及其磺酰胺的合成及晶体结构,有机化学,2006,26,82-86.
[6]Jr.Doibier,W.R.;Duan,J.X.;Roche,A.A novel,non-high-dilution method for preparation of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane,Organic Letter,2000,2,1867-1869.
[7]William,T.G.;Pittsburgh,P.Method for promoting aluminum chloride catalyzed isomerization of sym-octahydrophenthrene to sym-octahydroanthracene with aralkyl halide,US 4385194,1982.
[8]Zhang,X.L.;Li,M.Reductive coupling reaction of trihalomethylarenes using the TiCl_4-Ga system,Chinese Journal of Organic Chemistry,1999,19,300-303.
[9]Mataka,S.;Liu,G.B.;Sawada,T.;Kurisu,M.;Tashiro,M.Photothermal side-chain bromination of methyl-,dimethyl-,and trimethylbenzenes with N-bromosuccinimide,Bulletin of the Chemical Society of Japan,1994,67,1113-1119.
[10]Mataka,S.;Kurisu,M.;Takahashi,K.;Tashiro,M.The bromination of methylarenes with NBS by irradiation using a tungsten lamp.Preparation of benzotribromides,Chemistry Letter,1984,11,1969-1972.
[11]Moushy,M.Trifluoromethyl substituted biphenyls and diphenyl ethers,Journal of the American Chemical Society,1952,74,1858-1859.
[12]Zhang,Y.H.;Shibatomi,K.;Yamamoto,H.Lewis acid-catalyzed highly selective halogenation of aromatic compounds,SynLetter,2005,2837-2842.
[13]Hunter,W.H.;Edger,D.E.Carbon tetrabromide as a brominating agent,Journal of the American Chemical Society,1932,54,2025-2028.
[14]Richard,H.M.;Marcus,E.H.;Paul,M.G.Regularities in the densities of dilute solutions of some monochlorobenzotrihalides,Journal of the American Chemical Society,1954,76,4737-4739.
[15]Heble,L.S.;Nadkarni,D.R.;Wheele,T.S.Mixed laterally-halogenated toluenes,Journal of Chemistry Society,1938,1322-1323.
[16]Mark,S.B.;Manjushrmi,M.A convenient transformation of benzyl bromides into (2-bromoethynyl)benzenes,Journal of the Chemical Society,Chemical Communications,1979,563-564.
[17]Mark,S.B.;Anthonyg,W.B.Reaction of allyl bromides with bromoform and base under phase transfer conditions,Journal of the Chemical Society,Chemical Communications,1979,210-211.
[18]Attilio,C.;Roberto,S.;Anselmo,P.Benzylic bromination-acetoxylation of toluenes by bromide ion-catalyzed thermal decomposition of peroxydisulfate in acetic acid in the presence of acetate ions,Journal of Organic Chemistry,1987,52,4925-4927.
[19]Yagupol'skii,L.M.;Kondratenko,N.V.Exchange of halogen atoms in trihalomethyl groups,Zhurnal Organicheskoi Khimii,1967,37,1770-1775.
[20]Castaiier,J.;Riera,J.;Carilla,J.;Robert,A.;Molins,E.;Miravitllest,C.A new trifluoromethylating agent:Synthesis of polychlorinated(trifluoromethyl)benzenes and 1,3-bis(trifluoromethyl)benzenes and conversion into their trichloromethyl counterparts and molecular structure of highly strained polychloro-m-xylenes,Journal of Organic Chemistry, 1991,56,103-110.
[21]Riera,J.;Castaiier,J.;Carilla,J.;Robert,A.New synthese of polychloro(trifluoromethyl)benzenes and highly strained polychloro(trichloromethyl)benzenes,Tetrahedron Letters,1989,30,3825-3828.
[22]Bloodworth,A.J.;Bowyer,K.J.A mild convenient halogen-exchange route to difluorides and trifluorides,Tetrahedron Letters,1987,28,5347-5350.
[23]Prakash,G.K.Surya;Hu,J.B.;Simon,J.;Bellew,D.R.;Olah,G.A.Preparation of α,α-difluoroalkanesulfonic acids,Journal of Fluorine Chemistry,2004,125,595-601.
[24]潘良金,朱旭容.相转移催化剂在对硝基三溴苄合成中的应用,江苏化工,2003,31,28-30.
[25]陈红飙,林原斌,罗和安,陈冠凡,刘展鹏,廖云峰.芳酸及其衍生物的三氯甲基化反应的研究,有机化学,2005,25,532-535.
[26]赵辉,陈红飙,刘展鹏,苏琼,林原斌.三溴甲基芳烃合成新方法的研究,有机化学,2007,27,1250-1253.
[1]黄维垣,杜灿屏,朱士正.中国有机氟化学十年进展,北京:高等教育出版社,1998,p201.
[2]王飞,刘小莉,胡满成.氟化学的发展及应用,陕西师范大学学报,2000,17,101-103.
[3]徐国耀.特殊的化学领域-有机氟化学,化工生产与技术,1994,3,1-6.
[4]Frosco,M.B.;Lawrence,L.E.;Barret,J.F.~(37)th interscience conference on antimicrobial agents and chemotherapy(ICAAC),Expert Opinion on Investigational Drugs,1997,6,1951-1968.
[5]Bryskier,A.Novelties in the field of fluoroqinolones,Expert Opinion on Investigational Drugs,1997,9,1227-1245.
[6]Wen,J.;Yin,H.;Tian,M.;Chen,Q.Synthesis and mesomorphic properties of 4-n-alkoxy4'-[4-((4-n-alkoxy-2,3,5,6-tetrafluorophenyl)ethynyl)benzyloxy]benzoates,Liquid Crystal,1995,19,511-517.
[7]Chen,B.;Yank,Y.;Wen,J.Synthesis and mesomorphic properties of 4-(1,1,7-trihydroperfluoroheptyloxycarbon-yl)phenyl-4'-n-alkoxybiphenyl-4-carboxylate,Liquid Crystal,1998,24,539-543.
[8]Ruppert,I.Nucleophilic trifluoromethylation with the reagent combination(Et_2N)_3P/CF_3Br,Journal of Fluorine Chemistry,1985,29,98-103.
[9]Wakselman,C.;Tordeux,M.Mild trifluoromethylation of organic compounds,Industrial Chemistry Library,1996,8,313-324.
[10]Kischkewitz,J.;Naumann,D.Comparison of the trifluoromethylating properties of(CF_3)_2Hg,CF_3I and(CF_3)_2Te:Reactions with olefinic and aromatic compounds,Journal of Fluorine Chemistry,1985,29,73-87.
[11]Sawada,H.;Nakayama,M.;Yoshida,M.;Yoshida,T.;Kamigata,N.Trifluoromethylation of aromatic compounds with bis(trifluoroacetyl) peroxide,Journal of Fluorine Chemistry,1990,46,423-431.
[12]Kobayashi,Y.;Kumadaki,I.Trifluoromethylation of aromatic compounds,Tetrahedron Letters,1969,10,4095-4096.
[13]Marhold,A.;Klauke,E.A new method for the tdfluoromethylation of aromatic compounds,Journal of Fluorine Chemistry,1980,16,516-520.
[14]Marhold,A.;Klauke,E.A new method for the trifluoromethylation of aromatics,Journal of Fluorine Chemistry,1981,18,281-291.
[15]Umemoto,T.;Ando,A.Synthesis and reactivity of N-trifluoromethyl-N-nitrosotrifluoromethanesulfonamide as a new type of trifluoromethylating agent,Bulletin of the Chemical Society of Japan,1986,59,447-452.
[16]Umemoto,T.Twenty years in my fluorine chemistry,Journal of Fluorine Chemistry,2000,105,211-213.
[17]Prakash,G K.S.;Krishnamurti,R.;Olah,G.A.Synthetic methods and reactions.141.Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane(TMS-CF_3).A trifluoromethide equivalent,Journal of the American Chemical Society,1989,111,393-395.
[18]Iseki,K.;Nagai,T.;Kobayashi,Y.Asymmetric trifluoromethylation of aldehydes and ketones with trifluoromethyltrimethylsilane catalyzed by chiralquaternary ammonium fluorides,Tetrahedron Letter,1994,35,3137-3138.
[19]Urata,H.;Fuchikami,T.A novel and convenient method for trifluoromethylation of organic halides using CF_3SiR'_3/KF/Cu(I) system,Tetrahedron Letters,1991,32,91-94.
[20]Kitazume,T.;Nakajima,S.Introduction of several trifluoromethyl groups onto the activated aromatic materials with CF_3TMS-CuI-KF system,Journal of Fluorine Chemistry,2004,125,1447-1449
[21]Hagiwara,T.;Mochizuki,H.;Fuchikami,T.Unique reactivity of aminoketones in the trifluoromethylation with trialkyl(trifluoromethyl)silanes,Synletter,1997,587-588.
[22]Matsui,K.;Tobita,E.;Ando,M.;Kondo,K.A convenient trifluoromethylation of aromatic halides with sodium trifluoroacetate,Chemistry Letters,1981,10,1719-1920.
[23]Yukihisa,N.;Takeshi,H.Japanese Patent 0413651,1990.
[24]Cart,G.E.;Chambers,R.D.;Holmes,T.F.;Parker,D.G.Sodium perfluoroalkane carboxylates as sources of perfluoroalkyl groups,Journal of the Chemical Society,Perkin Transactions,1988,1,921-926.
[25]Freskos,J.W.A convenient synthesis of pentafluoroethyl-substituted aromatics,Synthetic Communications,1988,18,965-972.
[26]Langlois,B.R.;Roques,N.Nucleophilic trifluoromethylation of aryl halides with methyl trifluoroacetate,Journal of Fluorine Chemistry,2007,128,1318-1325.
[27]Long,Z.;Duan,J.;Lin,Y.;Guo,C.;Chen,Q.Potassium 3-oxa-o-fluorosulfonyl perfluoropentanoate(FO_2SF_2CF_2CF_2OCF_2COOK),a low-temperature trifluoromethylating agent for organic halides;its a-carbon-oxygen bond fragmentation,Journal of Fluorine Chemistry,1996,78,177-181.
[28]Chen,Q.;Wu,S.Studies on fluoroalkylation and fluoroalkoxylation.Part 33.Direct trifluoromethylation of aryl halides with fluorosulphonyldifluoromethyl iodide in the presence of copper:an electron transfer induced process,Journal of the Chemical Society,Perkin Transactions,1989,1,2385-2387.
[29]Chen,Q.;Wu,S.Methyl fluorosulphonyldifluoroacetate;a new trifluoromethylating agent,Journal of the Chemical Society,Chemical Communications,1989,1,705.
[30]Chen,Q.;Yang,G.;Wu,S.Copper electron-transfer induced trifluoromethylation with methyl fluorosulphonyldifluoroacetate,Journal of Fluorine Chemistry,1991,55,291-298.
[31]Chen,Q.;Duan,J.Methyl 3-oxo-fluorosulfonylperfluoropentanoate:a versatile trifluoromethylating agent for organic halides,Journal of the Chemical Society,Chemical Communications,1993,1,1389-1342.
[32]Su,D.;Duan,J.;Chen,Q.Methyl chlorodifluoroacetate a convenient trifluoromethylating agent,Tetrahedron Letter,1991,32,7689-7690.
[33]McNeil,J.G.;Burton,D.J.Generation of trifluoromethylcopper from chlorodifluoroacetate, Journal of Fluorine Chemistry,1991,55,225-227.
[34]Duan,J.;Su,D.;Chen,Q.Trifluoromethylation of organic halides with methyl halodifluoroacetates-a process via difluorocarbene and trifluoromethide intermediates,Journal of Fluorine Chemistry,1993,61,279-284.
[35]Chen Q.;Duan,J.Copper induced single electron transfer trifluorbmethylation of organic halides with 3-oxo-ω-fluorosulfonylperfluoropentyl iodide,Chinese Journal of Chemistry,1994,12,464-470.
[36]Clark,J.H.;McClinton,M.A.;Jones,C.W.;Landon,P.;Bishop,D.;Blade,R.J.The effect of charcoal on the trifluoromethylation of aryl chlorides using Button's reagent,Tetrahedron Letters,1989,30,2133-2136.
[37]Howarth,M.S.;Seovell,E.G.;Watson,D.J.Process for the preparation of fluoromethylpyridines,US Patent 4745193,1986.
[38]Fung,A.P.;Wilson,C.A.Preparation of(trifluoromethyl)pyridines under liquid phase conditions,US Patent 4590279,1983.
[39]Fung,A.P.Liquid phase halogen exchange of(trichloromethyl) pyridines to (trifluoromethyl)pyridines,US Patent 4567273,1984.
[40]Erich,K.Fluorination of trichloromethyl groups,US Patent 4079089,1978.
[41]Murray,R.L.;Beanblossom,W.S.;Wojcik,B.H.Production of bis(Trifluoromethyl)benzene,Industrial and Engineering Chemistry,1947,39,302-305.
[42]Smith,W.C.Reaction of SF_4 with organic compounds containing a carbonyl radical,US Patent 2859245,1958.
[43]Ishida,M.;Koide,M.;Katsuhara,Y.Method for producing bis(trifluoromethyl)benzene,US Patent 6093858,2000.
[44]Marhold,A.;Kaethe,B.Method for producting trifluoromethylanilines,Japanese Patent 2001151736,2001.
[45]王秋玲.3,4-二氯三氟甲苯的合成方法,农药,1995,34,23-24.
[46]匡平.含氟芳香族化合物的合成及应用,辽宁化工,1992,12,47-52.