摘要/Abstract

[3,3] σ迁移反应作为有机化学中的经典反应, 自发现以来, 反应类型不断扩大, 且一直广泛应用于有机与药物合成等领域. 因为羟胺衍生物的N—O键强度较弱, 较易断裂, [3,3] σ迁移反应在较为温和的条件下即可进行, 得到含有羟基和氨基的复杂分子, 近年来, 该类反应引起越来越多的关注. 综述了羟胺衍生物的[3,3] σ迁移反应, 包括N-芳
关键词: [3,3] σ迁移, 羟胺衍生物, 重排, 亲核反应, N—O键
[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


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