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

Hong Min Kang; Young Kwan Lim; In Jee Shin; Hee Yeon Kim; Cheon Gyu Cho

doi:10.1021/ol060451+

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

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

Dept. of Fine Chemistry

Hanyang University

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2047-2050
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol060451+
State	Published - 11 May 2006

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

abstract = "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.",

author = "Kang, \{Hong Min\} and Lim, \{Young Kwan\} and Shin, \{In Jee\} and Kim, \{Hee Yeon\} and Cho, \{Cheon Gyu\}",

year = "2006",

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doi = "10.1021/ol060451+",

language = "English",

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journal = "Organic Letters",

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T1 - Regioselective [5,5]-sigmatropic rearrangement reactions of aryl hydrazides

AU - Kang, Hong Min

AU - Lim, Young Kwan

AU - Shin, In Jee

AU - Kim, Hee Yeon

AU - Cho, Cheon Gyu

PY - 2006/5/11

Y1 - 2006/5/11

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/33744741355

U2 - 10.1021/ol060451+

DO - 10.1021/ol060451+

M3 - Article

AN - SCOPUS:33744741355

SN - 1523-7060

VL - 8

SP - 2047

EP - 2050

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

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

Abstract

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