Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3002-3014.DOI: 10.6023/cjoc202103022 Previous Articles     Next Articles


羟胺衍生物的[3,3] σ迁移反应及其应用

张广宇, 许家喜*()   

  1. 北京化工大学化学学院有机化学系 化工资源有效利用国家重点实验室 北京 100029
  • 收稿日期:2021-03-11 修回日期:2021-04-11 发布日期:2021-05-08
  • 通讯作者: 许家喜
  • 基金资助:

[3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives

Guangyu Zhang, Jiaxi Xu()   

  1. State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029
  • Received:2021-03-11 Revised:2021-04-11 Published:2021-05-08
  • Contact: Jiaxi Xu
  • Supported by:
    National Natural Science Foundation of China(21772010)

[3,3] σ shift is one of classic reactions in organic chemistry. Since its discovery, the reactions have been expanding to different types and widely used in the fields of organic and pharmaceutical synthesis. Because the N—O bond strength of hydroxylamine derivatives is weak and easy to break, their [3,3] σ shift can be carried out under mild conditions to afford complex molecules containing hydroxyl and amino groups. In recent years, more and more attention has been paid to these reactions. The [3,3] σ shift rearrangements of hydroxylamine derivatives, including N-aryl-O-alkenylhydroxylamines, N,O-diaryl hydroxylamines, N,O-dialkenyloxyamines, N-alkenyl-O-arylhydroxyamines, and N-alkyl-O-acylhydroxyamines are reviewed, and a new prospect for the [3,3] σ shifts of hydroxylamine derivatives and their future development are put forward.

Key words: [3,3] σ shift, hydroxylamine, rearrangement, nucleophilic reaction, N—O bond