羟胺衍生物的[3,3] σ迁移反应及其应用
收稿日期: 2021-03-11
修回日期: 2021-04-11
网络出版日期: 2021-05-08
基金资助
国家自然科学基金(21772010)
[3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives
Received date: 2021-03-11
Revised date: 2021-04-11
Online published: 2021-05-08
Supported by
National Natural Science Foundation of China(21772010)
张广宇 , 许家喜 . 羟胺衍生物的[3,3] σ迁移反应及其应用[J]. 有机化学, 2021 , 41(8) : 3002 -3014 . DOI: 10.6023/cjoc202103022
[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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