摘要
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.
A novel synthesis of aromatic aldehyde from arylmethyl azides has been explored via base-mediated N_2-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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2017年第1期97-102,共6页
Chinese Journal of Organic Chemistry
基金
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~~
关键词
芳甲基叠氮
脱氮
芳醛
叔丁醇钾
arylmethyl azides
N_2-extrusion
aryl aldehydes
t-BuOK
