Vinylogous Wolff rearrangement. 4. General reaction of. beta.,. gamma.-unsaturated. alpha.'-diazo ketones

AB Smith III, BH Toder, SJ Branca

Index: Smith, Amos B.; Toder, Bruce H.; Branca, Stephen J. Journal of the American Chemical Society, 1984 , vol. 106, # 14 p. 3995 - 4001

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Citation Number: 33

Abstract

Abstract: The preparation and vinylogous Wolff rearrangement (VWR) of some 21 acyclic and monocyclic 0, y-unsaturated a'-diazo ketones are described. The resulting y, &unsaturated esters are summarized in Tables I-VI. The rearrangement is promoted by CuS04, Cu (AcAc),, or Cu (OTf), in the presence of various alcohols and is postulated to involve insertion of the diazo carbon into the (3, y-olefinic bond to form a bicyclo [2.1. O] ...