An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides

Benjamin F. Strick; Devon A. Mundal; Regan J. Thomson

doi:10.1021/ja2066219

An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides

Benjamin F. Strick, Devon A. Mundal, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

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

24 Scopus citations

Abstract

The development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via singlet N-nitrene intermediates, is reported. The requisite allylic hydrazide precursors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene. The products of this novel transformation are shown to be useful precursors to a variety of compounds.

Original language	English (US)
Pages (from-to)	14252-14255
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	36
DOIs	https://doi.org/10.1021/ja2066219
State	Published - Sep 14 2011

ASJC Scopus subject areas

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja2066219

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title = "An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides",

abstract = "The development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via singlet N-nitrene intermediates, is reported. The requisite allylic hydrazide precursors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene. The products of this novel transformation are shown to be useful precursors to a variety of compounds.",

author = "Strick, {Benjamin F.} and Mundal, {Devon A.} and Thomson, {Regan J.}",

year = "2011",

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AU - Mundal, Devon A.

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Y1 - 2011/9/14

N2 - The development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via singlet N-nitrene intermediates, is reported. The requisite allylic hydrazide precursors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene. The products of this novel transformation are shown to be useful precursors to a variety of compounds.

AB - The development of an efficient oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides, via singlet N-nitrene intermediates, is reported. The requisite allylic hydrazide precursors are readily prepared and undergo smooth sigmatropic rearrangement upon exposure to iodosobenzene. The products of this novel transformation are shown to be useful precursors to a variety of compounds.

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An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides

Abstract

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CCDC 855131: Experimental Crystal Structure Determination

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An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 855131: Experimental Crystal Structure Determination

Cite this