SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 04: 765 - 769

DOI: https://doi.org/10.6023/cjoc1109223

研究简报

微波对烯丙基芳醚的Claisen 重排反应影响研究

  • 兰聪 ,
  • 徐盼 ,
  • 梁荣辉 ,
  • 许泽龙 ,
  • 夏之宁
展开
  • 重庆大学化学化工学院 重庆 400030

收稿日期: 2011-09-22

  修回日期: 2011-12-11

  网络出版日期: 2012-04-24

基金资助

科技部国际合作(No. 2010DFA32680)资助项目.

收起

Study on the Microwave Effect in the Claisen Rearrangement of the Allyl Phenyl Ethers

  • Lan Cong ,
  • Xu Pan ,
  • Liang Ronghui ,
  • Xu Zelong ,
  • Xia Zhining
Expand
  • College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030

Received date: 2011-09-22

  Revised date: 2011-12-11

  Online published: 2012-04-24

Supported by

Project supported by the International Science and Technology Cooperation Program of China (No. 2010DFA32680).

Fold

摘要

5 种烯丙基芳醚衍生物在无溶剂、无催化剂的条件下进行Claisen 重排反应, 采用了微波加热和常规加热方式, 比较了同等温度下微波加热和常规加热反应速率的差异. 结果表明微波加热可以显著提高烯丙基苯醚Claisen 重排反应的速率. 反应温度为190 ℃时, 微波加热下反应速率可提高5～10 倍. 微波加热是一种无催化剂、高产率的Claisen 重排反应的方法.

关键词： 无溶剂; 无催化; Claisen 重排; 微波辅助合成; 烯丙基芳醚

本文引用格式

兰聪 , 徐盼 , 梁荣辉 , 许泽龙 , 夏之宁 . 微波对烯丙基芳醚的Claisen 重排反应影响研究[J]. 有机化学, 2012 , 32(04) : 765 -769 . DOI: 10.6023/cjoc1109223

Abstract

Solvent-free and catalyst-free Clasien rearrangement of five kinds of allyl phenyl ethers were investigated under microwave heating and conventional heating respectively. The effects on the reaction rates by microwave heating and conventional heating were compared. The results demonstrate that microwave heating could greatly accelerate the reaction rate of the Claisen rearrangement. The reaction rates under microwave heating are 5～10 times higher than those acted by conventional heating at 190 ℃. The microwave heating is an efficient method of catalyst-free, high yield of Claisen rearrangement.

Key words： solve-free; catalyst-free; Claisen rearrangement; microwave assisted synthesis; allyl phenyl ether

参考文献

[1] Liu, Z. H.; Qu, H. C.; Gu, X. Y.; Lee, K. S.; Bryan, G.; Kumirov, V. K.; Hruby, V. J. Tetrahedron Lett. 2010, 51(27), 3518.

[2] Bruder, M.; Smith, S. J.; Blake, A. J.; Moody, C. J. Org. Biomol. Chem. 2009, 7(10), 2127.  

[3] Camp, J. E.; Craig, D. Tetrahedron Lett. 2009, 50(26), 3503.

[4] Biswas, S.; Maiti, S.; Jana, U. Eur. J. Org. Chem. 2010, 41(39), 2861.

[5] Ollevier, T.; Mwene-Mbeja, T. M. Tetrahedron Lett. 2006, 47(24), 4051.

[6] Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 2002(9), 1461.  

[7] Wang, S. L.; Cheng, C.; Gong, F.; Wu, F. Y.; Jiang, B.; Zhou, J. F.; Tu, S. J. Chin. J. Chem. 2011, 29, 2101.

[8] Andrade, M. M. J. Comb. Chem. 2010, 12(2), 245.  

[9] Ye, P.; Sargent, K.; Stewart, E.; Liu, J. F.; Yohannes, D.; Yu, L. B. J. Org. Chem. 2006, 71(8), 3137.

[10] Gao, R.; Canney, D. J. J. Org. Chem. 2010, 75(21), 7451.

[11] Chai, H. S.; Lam, Y. L. J. Comb. Chem. 2010, 12(2), 286.  

[12] Chebanov, V. A.; Muravyova, E. A.; Desenko, S. M.; Musatov, V. I.; Knyazeva, I. V.; Shishkina, S. V.; Shishkin, O. V.; Kappe, C. O. J. Comb. Chem. 2006, 8(3), 427.

[13] Yamashitaa, H.; Mitsukuraa, Y.; Kobashia, H.; Hirokia, K.; Sugiyamaa, J. I.; Onishib, K.; Sakamotoc, T. Appl. Catal., A 2010, 381(1～2), 145.

[14] Yamamoto, T.; Enokida, H.; Fujimoto, M. Green Chem. 2003, 5(6), 690.

[15] Schobert, R.; Gordon, G. J.; Mullen, G.; Stehle, R. Tetrahedron Lett. 2004, 45(6), 1121.

[16] Chen, X. X.; Xu, P.; Xia, Z. N. Chemistry 2009, (8), 674 (in Chinese). (陈新秀, 徐盼, 夏之宁, 化学通报, 2009, (8), 674.)

[17] Pincock, A. L.; Pincock, J. A.; Stefanova, R. J. Am. Chem. Soc. 2002, 124(33), 9768.  

[18] Willem, A. L. V. O.; Garreth, L. M.; Lee, G. M.; Samuel, K.; Simon, S. M.; Natalie, T.; Charles, B. D. K. Tetrahedron 2005, 61(32), 7746.
Options
文章导航

/

〈 〉