Journal of the American Chemical Society

A general method for the synthesis of amines by the rearrangement of allylic trichloroacetimidates. 1, 3 Transposition of alcohol and amine functions

LE Overman

Index: Overman,L.E. Journal of the American Chemical Society, 1976 , vol. 98, p. 2901 - 2910

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Citation Number: 337

Abstract

Abstract: A new synthetic method for the preparation of amines is reported (Scheme I). Allylic alcohols are condensed with trichloroacetonitrile to yield the corresponding allylic trichloroacetimidic esters (3). Thermolysis of 3 at 25-140 OC results in allylic rearrangement to afford the corresponding trichloroacetamide 4. To complete the l, 3 conversion of a hydroxy to a primary amino group, the trichloroacetyl group can be removed by treatment ...