有机化学 ›› 2017, Vol. 37 ›› Issue (1): 97-102.DOI: 10.6023/cjoc201605045 上一篇    下一篇

研究论文

叔丁醇钾催化芳甲基叠氮化合物合成芳醛和芳酮的反应研究

黄青兰, 谭志强, 于长江, 朱晓敏, 吴禄勇   

  1. 海南师范大学热带药用植物化学教育部重点实验室 海口 571158
  • 收稿日期:2016-05-30 修回日期:2016-08-14 发布日期:2016-09-22
  • 通讯作者: 吴禄勇 E-mail:wuluyong@hainnu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21362008)、海南省大学生创新创业训练计划(No. 20140062)资助项目.

Research for the t-BuOK-Catalyzed Synthesis of Aromatic Aldehydes and Ketone from Arylmethyl Azides

Huang Qinglan, Tan Zhiqiang, Yu Changjiang, Zhu Xiaoming, Wu Luyong   

  1. Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158
  • Received:2016-05-30 Revised:2016-08-14 Published:2016-09-22
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China(No. 21362008) and the Undergraduate Innovation and Entrepreneurship Training Program of Henan Province(No. 20140062).

对叔丁醇钾参与下芳甲基叠氮发生脱氮、水解反应进行了深入研究,得到芳甲醛.实验中,探讨了碱、水解条件、溶剂及碱量对苯甲醛反应产率的影响.研究发现,以N,N-二甲基甲酰胺(DMF)为溶剂,以叔丁醇钾(t-BuOK)为碱,反应效果最佳,以83%的产率得到苯甲醛.同时,对不同结构的叠氮化合物进行了考察,取代苯甲基叠氮能够顺利反应,得到相应的芳醛和芳酮,产率38%~87%,其他芳甲基叠氮化合物反应效果差.根据控制实验,探讨了反应机理.

关键词: 芳甲基叠氮, 脱氮, 芳醛, 叔丁醇钾

A novel synthesis of aromatic aldehyde from arylmethyl azides has been explored via base-mediated N2-extrusion and hydrolyzation.The effects of bases,hydrolysis conditions and the amount of base used on the reaction were also investigated.Benzaldehyde was isolated in the best yield of 83%,when the reaction was carried in N,N-dimethylformamide(DMF) and catalyzed by t-BuOK.Meanwhile,a variety of azides were investigated,and it was found that substituted benzyl azides could give the corresponding aromatic aldehydes in the yield of 38%~87%.The reaction of heteoaryl methyl azides was less efficient.According to the controlling experiments,the mechanism has been quitted.

Key words: arylmethyl azides, N2-extrusion, aryl aldehydes, t-BuOK