An Oxidative [2, 3]-Sigmatropic Rearrangement of Allylic Hydrazides

BF Strick, DA Mundal, RJ Thomson

Index: Strick, Benjamin F.; Mundal, Devon A.; Thomson, Regan J. Journal of the American Chemical Society, 2011 , vol. 133, # 36 p. 14252 - 14255

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Citation Number: 15

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.