An oxidative [2,3]-sigmatropic rearrangement of allylic hydrazides |
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Authors: | Strick Benjamin F Mundal Devon A Thomson Regan J |
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Affiliation: | Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA. |
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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. |
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