过氧化氢在有机合成中的几个应用
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摘要
本论文一共分为四个部分:第一章过氧化氢在有机合成中的应用进展
本章归纳了过氧化氢促进烯烃的环氧化、醇的选择氧化、硫化物到砜的转化、有机物的卤化等反应。所引用的文献都是国际重要期刊文献。第二章H_2O_2/V_2O_5催化体系促进汉斯酯1,4-二氢吡啶的芳构化
我们以醛、乙酰乙酸乙酯、醋酸铵为原料,在80℃条件下,一锅煮合成了一系列的汉斯酯1,4-二氢吡啶化合物,该合成方法对环境友好。在考察过氧化氢芳构化汉斯酯1,4-二氢吡啶的过程中,我们尝试了多种催化剂来完成该反应。本章我们运用H_2O_2/V_2O_5体系在室温下完成汉斯酯1,4-二氢吡啶的芳构化,并且为本反应提出一个可能的反应机理。本反应使用的试剂价廉易得,反应条件温和,产物收率较高,该方法是对已有方法的一种有益补充。第三章H_2O_2/Ti(SO_4)_2催化体系促进汉斯酯1,4-二氢吡啶的芳构化
我们使用5 mol%的Ti(SO_4)_2催化过氧化氢完成一系列汉斯酯1,4-二氢吡啶的芳构化,产物收率较高。反应过程中,我们考察了溶剂对反应的影响,最后选择乙腈做为该反应的溶剂。该反应在室温下进行8 h,所有的底物都可以转化为相应的产物。反应所用的催化剂和氧化剂便宜易得。第四章H_2O_2/Ti(SO_4)_2体系选择氧化醇的研究
本章我们成功运用H_2O_2/Ti(SO_4)_2体系完成醇的选择性氧化。除了苯甲醇和对硝基苯甲醇收率不好之外,其它醇的氧化产物都得到很好的收率。
本论文拓展了过氧化氢在有机合成中的应用,扩大了催化剂Ti(SO_4)_2、V_2O_5在有机合成中的应用范围,具有一定的参考价值。
In this thesis, the following four parts are mainly included: ChapterⅠ: Recent progress of hydrogen peroxide in organic synthesis
In this chapter, epoxidation of alkenes, selective oxidation of alcohols, oxidation of sulfides to sulfoxides and sulphones, halogenation of organic compounds carried out using hydrogen peroxide were summarized. The references all were published in leading international journals. ChapterⅡ: Aromatization of Hantzsch 1,4-dihydropyridines by H_2O_2/V_2O_5
A series of Hantzsch 1,4-dihydropyridines were synthesized in an environmentally benign method , by reacting aldehydes with acetoacetate esters and ammonium acetate at 80℃. We have chosed several catalysts and found that H_2O_2/V_2O_5 was a good system for the aromatization of Hantzsch 1,4-dihydropyridines to the correspondence pyridines. A possible reaction mechanism was also suggested. The cheapness, easy availability of the reagents, mild reaction conditions as well as excellent yields of the products are the advantages which make this protocol a useful addition to the existing methodologies. ChapterⅢ: Aromatization of Hantzsch 1,4-dihydropyridines by H_2O_2/Ti(SO_4)_2
Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by a catalytic amount (5mol%) of Ti(SO_2)_2 with H_2O_2 to afford the corresponding pyridine derivatives in high yields. Various solvent systems were tested. All the reactions were carried out in acetonitrile at room temperature for eight hours to complete conversion of the substrates. The cheapness of the catalyst and the oxidizer were employed. ChapterⅣ: Selective oxidation of alcohols to aldehydes and ketones with H_2O_2/Ti(SO_2)_2
In this chapter, the selective oxidation of alcohols to aldehydes and ketones with H_2O_2/Ti(SO_4)_2 have been accomplished. All of the substrates gave the excellent yields except the p-nitrobenzyl alcohol and the benzyl alcohol.
The above results reference values in enlarging the application field of hydrogen peroxide in organic synthesis. We think that the use of V_2O_5 and Ti(SO_4)_2 catalysts with hydrogen peroxide in organic synthesis were worth to being referred.
本章归纳了过氧化氢促进烯烃的环氧化、醇的选择氧化、硫化物到砜的转化、有机物的卤化等反应。所引用的文献都是国际重要期刊文献。第二章H_2O_2/V_2O_5催化体系促进汉斯酯1,4-二氢吡啶的芳构化
我们以醛、乙酰乙酸乙酯、醋酸铵为原料,在80℃条件下,一锅煮合成了一系列的汉斯酯1,4-二氢吡啶化合物,该合成方法对环境友好。在考察过氧化氢芳构化汉斯酯1,4-二氢吡啶的过程中,我们尝试了多种催化剂来完成该反应。本章我们运用H_2O_2/V_2O_5体系在室温下完成汉斯酯1,4-二氢吡啶的芳构化,并且为本反应提出一个可能的反应机理。本反应使用的试剂价廉易得,反应条件温和,产物收率较高,该方法是对已有方法的一种有益补充。第三章H_2O_2/Ti(SO_4)_2催化体系促进汉斯酯1,4-二氢吡啶的芳构化
我们使用5 mol%的Ti(SO_4)_2催化过氧化氢完成一系列汉斯酯1,4-二氢吡啶的芳构化,产物收率较高。反应过程中,我们考察了溶剂对反应的影响,最后选择乙腈做为该反应的溶剂。该反应在室温下进行8 h,所有的底物都可以转化为相应的产物。反应所用的催化剂和氧化剂便宜易得。第四章H_2O_2/Ti(SO_4)_2体系选择氧化醇的研究
本章我们成功运用H_2O_2/Ti(SO_4)_2体系完成醇的选择性氧化。除了苯甲醇和对硝基苯甲醇收率不好之外,其它醇的氧化产物都得到很好的收率。
本论文拓展了过氧化氢在有机合成中的应用,扩大了催化剂Ti(SO_4)_2、V_2O_5在有机合成中的应用范围,具有一定的参考价值。
In this thesis, the following four parts are mainly included: ChapterⅠ: Recent progress of hydrogen peroxide in organic synthesis
In this chapter, epoxidation of alkenes, selective oxidation of alcohols, oxidation of sulfides to sulfoxides and sulphones, halogenation of organic compounds carried out using hydrogen peroxide were summarized. The references all were published in leading international journals. ChapterⅡ: Aromatization of Hantzsch 1,4-dihydropyridines by H_2O_2/V_2O_5
A series of Hantzsch 1,4-dihydropyridines were synthesized in an environmentally benign method , by reacting aldehydes with acetoacetate esters and ammonium acetate at 80℃. We have chosed several catalysts and found that H_2O_2/V_2O_5 was a good system for the aromatization of Hantzsch 1,4-dihydropyridines to the correspondence pyridines. A possible reaction mechanism was also suggested. The cheapness, easy availability of the reagents, mild reaction conditions as well as excellent yields of the products are the advantages which make this protocol a useful addition to the existing methodologies. ChapterⅢ: Aromatization of Hantzsch 1,4-dihydropyridines by H_2O_2/Ti(SO_4)_2
Hantzsch 1,4-dihydropyridines undergo smooth aromatization catalyzed by a catalytic amount (5mol%) of Ti(SO_2)_2 with H_2O_2 to afford the corresponding pyridine derivatives in high yields. Various solvent systems were tested. All the reactions were carried out in acetonitrile at room temperature for eight hours to complete conversion of the substrates. The cheapness of the catalyst and the oxidizer were employed. ChapterⅣ: Selective oxidation of alcohols to aldehydes and ketones with H_2O_2/Ti(SO_2)_2
In this chapter, the selective oxidation of alcohols to aldehydes and ketones with H_2O_2/Ti(SO_4)_2 have been accomplished. All of the substrates gave the excellent yields except the p-nitrobenzyl alcohol and the benzyl alcohol.
The above results reference values in enlarging the application field of hydrogen peroxide in organic synthesis. We think that the use of V_2O_5 and Ti(SO_4)_2 catalysts with hydrogen peroxide in organic synthesis were worth to being referred.
引文
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[6].Al-Maksoud W.,Daniele S.,Sorokin A.B.Practical oxidation of sulfides to sulfones by H_2O_2 catalysed by titanium catalyst[J].Green Chem.2008,10,447-451.
[7].Campeanu V.,Hardacre C,Parvulescu V.I.Stabilization of Ti-molecular sieve catalysts used in selective sulfoxidation reactions by ionic liquids[J].Green Chem.2008,7,326,332.
[8].Massa A.,De Lorenzo E.M.,Polymeric Ti(Ⅳ) glycolate:A heterogeneous catalyst for solvent-free sulfoxidation by t-butyl hydroperoxid[J].J.Mol.Catal.A:Chem.2006,250,27-29.
[9].Drug E.,Gozin M.Catalytic Oxidation of Hydrazo Derivatives Promoted by a TiCl_3/HBr System[J].J.Am.Chem.Soc.2007,129,13784-13785.
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[1].Urabe H.,Mitsui K.,Ohta S.et al.Titanium Alkoxide Complex of Functionalized Conjugated Dienes.A Versatile Bis-anionic Template for Stereoselective Construction of Carbon Frameworks[J].J.Am.Chem.Soc.2003,125,6074-6075.
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[9].Drug E.,Gozin M.Catalytic Oxidation of Hydrazo Derivatives Promoted by a TiCl_3/HBr System[J].J.Am.Chem.Soc.2007,129,13784-13785.
[1]. Iwahama T., Sakaguchi S., Nishiyama Y. et al. Aerobic Oxidation of Alcohols to Carbonyl Compounds Catalyzed by N-Hydroxyphthalimide (NHPI) Combined with Co(acac)_3 [J]. Tetrahedron Lett. 1995, 36, 6923-6926.
[2]. Iwahama T., Yoshino Y., Keitoku T. et al. Efficient OxidatioN of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-HydroxyphthAlimide Combined with a Co Species [J]. J. Org. Chem. 2000, 65, 6502-6407.
[3]. Semmelhack M. F., Schmid C. R., Cortes D. A. et al. Oxidation of Alcohols to Aldehydes with Oxygen and Cupric Ion, Mediated by NitrosoniuM Ion [J]. J. Am. Chem. Soc.1984, 106, 3374-3376.
[4]. a) Marko I. E., Gautier A., Dumeunier R. et al. Efficient, Copper-Catalyzed, Aerobic Oxidation of Primary Alcohols [J]. Angew. Chem. Int. Ed. 2004, 43, 1588-1591. b) Marko I. E., Gautier A., Mutonkole J. L. et al. Neutral, non-racemising catalytic aerobic oxidation of alcohols [J] J. Organomet. Chem. 2001, 624, 344-347. c) Marko I. E., Giles P. R., Tsukazaki M. Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative [i].Science 1996, 274, 2044-2046.
[5]. Zhu M. X., Li B. D., He P. Oxidant-dependent selective oxidation of alcohols utilizing multinuclear copper-triethanolamine complexes [J]. Tetrahedron 2008, 64, 9239-9243.
[6]. Martin S. E., Suarez D. F. Catalytic aerobic oxidation of alcohols by Fe(NO_3)_3-FeBr_3 [J]. Tetrahedron Lett. 2002, 43, 4475-4479.
[7]. Wang N., Liu R., Chen J. et al. NaNO_3-activated, iron-TEMPO catalyst system for aerobic alcohol oxidation under mild conditions [J]. Chem. Commun. 2005, 5322-5324.
[8]. Jiang N., Ragauskas A. J. TEMPO-catalyzed oxidation of benzylic alcohols to aldehydes with the H_2O_2/HBr/ionic liquid [bmim]PF_6 system [J]. Tetrahedron Lett. 2005, 46, 3323-3326.
[9]. Chhikara, B. S., Chandra, R., Tandon, V. A Versatile Method for the Hydrogen Peroxide Oxidation of Alcohols Using PTC Condition in tert-Butanol. [J]. Synlett 2005, 872-874.
[10]. Li C, Zheng P., Li J. The Dual Roles of Oxodiperoxovanadate Both as a Nucleophile and an Oxidant in the Green Oxidation of Benzyl Alcohols or Benzyl Halides to Aldehydes and Ketones [J]. Angew. Chem. Int. Ed., 2003, 42, 5063-5066.
[11]. Wang J., Yan L., Qian G. et al. Na_4H_3[SiW_9Al_3(H_2O)_3O_(37)]·12H_2O/H_2O: a new system for selective oxidation of alcohols with H_2O_2 as oxidant [J]. Tetrahedron 2007, 63, 1826-1832.
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