Regioselective [5,5]-sigmatropic rearrangement reactions of aryl hydrazides

  • Kang, Hong-Min
  • Lim, Young-Kwan
  • Shin, In-Jee
  • Kim, Hee-Yeon
  • Cho, Cheon-Gyu
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초록

N,N'-Aryl hydrazides with substituents at the ortho or meta positions undergo highly regioselective [5,5]-sigmatropic rearrangement reactions to furnish benzidines in good to excellent isolated yields. The presence of single substituent at either the ortho or meta position provides sufficient bias, effectively suppressing the formation of diphenylene, the major byproduct of the conventional benzidine rearrangement reaction.

키워드

BENZIDINE REARRANGEMENTEFFICIENT SYNTHESISMECHANISMAZOBENZENESWALLACH
제목
Regioselective [5,5]-sigmatropic rearrangement reactions of aryl hydrazides
저자
Kang, Hong-MinLim, Young-KwanShin, In-JeeKim, Hee-YeonCho, Cheon-Gyu
DOI
10.1021/ol060451+
발행일
2006-05
유형
Article
저널명
Organic Letters
8
10
페이지
2047 ~ 2050