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2012 , Vol. 32 >Issue 06: 1126 - 1130

DOI: https://doi.org/10.6023/cjoc1111023

研究简报

一种切断酰胺C—N 键的简便方法

  • 魏莹菲 ,
  • 史大昕 ,
  • 魏真 ,
  • 徐娟 ,
  • 李加荣
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  • 北京理工大学化工与环境学院 北京 100081

收稿日期: 2011-11-02

  修回日期: 2011-12-20

  网络出版日期: 2012-02-27

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A Convenient Method for Cleavage of Amide C—N Bond

  • Wei Yingfei ,
  • Shi Daxing ,
  • Wei Zhen ,
  • Xu Juan ,
  • Li Jiarong
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  • School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081

Received date: 2011-11-02

  Revised date: 2011-12-20

  Online published: 2012-02-27

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摘要

研究了一种质子酸和Lewis 酸共同催化酰胺C—N 键断键的新方法, 讨论了温度, CuCl2 量以及Lewis 酸种类对C—N 键断键率的影响, 并提出了在此条件下酰胺C—N 键断裂的可能机理. 新方法反应温度低、耗酸量小、条件温和.

关键词： 酰胺; 催化; Lewis 酸; C—N 键断裂

本文引用格式

魏莹菲 , 史大昕 , 魏真 , 徐娟 , 李加荣 . 一种切断酰胺C—N 键的简便方法[J]. 有机化学, 2012 , 32(06) : 1126 -1130 . DOI: 10.6023/cjoc1111023

Abstract

A new method for the cleavage of amide C—N bond was studied in this paper. Some factors such as reaction temperature, quantity of CuCl2 and kind of Lewis acid affected the cleavage of amide C—N bond are discussed. And the possible mechanism of C—N bond broken is proposed. This new method possesses lower temperature, less acid and milder conditions.

Key words： amide; catalysis; Lewis acid; cleavage of C—N bond

参考文献

[1] Loutfy, R. O.; Hsiao, C. K.; Kazmaier, P. M. Photogr. Sci. Eng.1983, 27, 5.
[2] Mujika, J. I.; Mercero, J. M.; Lopez, X. J. Am. Chem. Soc. 2005,127, 4445.  
[3] Zhang, Y. H.; Zhu, X. T.; Zhang, Q. P. Spec. Petrochem. 2009, 26,15 (in Chinese).(张跃华, 朱西挺, 张其平, 精细石油化工, 2009, 26, 15.)
[4] Anderson, G. W.; Blodinger, J.; Welcher, A. D. J. Am. Chem. Soc.1952, 74, 5309.  
[5] Ishai, D. B.; Berger, A. J. Org. Chem. 1952, 17, 1564.  
[6] (a) Fasman, G. D.; Blout, E. R. J. Am. Chem. Soc. 1960, 82, 2262.(b)Fujiwara, S.; Moerinaga, S.; Narita, K. Bull. Chem. Soc. Jpn.1962, 35, 438.(c) Albertson, N. F.; Mckay, F. C. J. Am. Chem. Soc. 1953, 73,5323.(d) Guttmann, S.; Boissonnas, R. A. Helv. Chim. Acta 1959, 42,1257.  
[7] Meienhofer, J.; Schnabel, E. Z. Naturforsch. 1965, 20B, 661.  
[8] Jaume, C.; Santiago, G. G.; Vicente, G.; Angel, G. F.; Amparo, L.;Marcial, M. M.; Adelina, V. Tetrahedron: Asymmetry 2000, 11,4549.  
[9] Pierfrancesco, B.; Silvia, C. Tetrahedron 1999, 55, 3025.  
[10] Coleman, D. R.; Royer, G. P. J. Org. Chem. 1980, 45, 2268.  
[11] Hendry, P.; Sargeson, A. M. J. Am. Chem. Soc. 1989, 111, 2521.  
[12] Erxleben, A. Inorg. Chem. 2005, 44, 1082.  
[13] Reddy, K. V.; Jacobson, A. R.; Kung, J. I. Inorg. Chem. 1991, 30,3520.  
[14] (a) Zhang, X. X.; Li, W. D. Chin. J. Org. Chem. 2003, 23, 1185 (inChinese).(张兴贤, 李卫东, 有机化学, 2003, 23, 1185.)(b) Qi, X. Y.; Wu, L.; Wang, J. G. Chin. J. Org. Chem. 2010, 30,1944 (in Chinese).(齐小燕, 伍林, 王建国, 有机化学, 2010, 30, 1944.)
[15] (a) Groves, J. T., Baron, L. A. J. Am. Chem. Soc. 1989, 111, 5442.(b) Deng, W.; Liu, L.; Guo, Q. X. Chin. J. Org. Chem. 2004, 24,150 (in Chinese).(邓维, 刘磊, 郭庆祥, 有机化学, 2004, 24, 150.)
[16] (a) Suh, J. H.; Chei W. S. Curr. Opin. Chem. Biol. 2008, 12, 207.(b) Li, L. S.; Wu, Y. L. Chin. J. Org. Chem. 2000, 20, 689 (in Chinese).(李连生, 吴毓林, 有机化学, 2000, 20, 689.)
[17] Erxleben, A. Inorg. Chem. 2005, 44, 1082.  
[18] Sayre, L. M. J. Am. Chem. Soc. 1986, 108, 1632.  
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