Rearrangements of Substituted 3-Aza-1, 2, 5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction

…, AB Hoem, CS McDonough

Index: Walters, Michael A.; Hoem, Andrew B.; McDonough, Colleen S. Journal of Organic Chemistry, 1996 , vol. 61, # 1 p. 55 - 62

Full Text: HTML

Citation Number: 17

Abstract

An investigation of the [3, 3]-sigmatropic reaction of substituted 3-aza-1, 2, 5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile ...