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Org Lett. 2006 May 11;8(10):2047-50.

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

Author information

1
Department of Chemistry, Hanyang University, Seoul, Korea.

Abstract

[reaction: see text] 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.

PMID:
16671778
DOI:
10.1021/ol060451+

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