Rearrangement of 1-methyl-2-(substituted-phenyl) piperidinium 1-methylides in a neutral medium

N Shirai, F Sumiya, Y Sato, M Hori

Index: Shirai, Naohiro; Sumiya, Fumihiko; Sato, Yoshiro; Hori, Mikiko Journal of Organic Chemistry, 1989 , vol. 54, p. 836 - 840

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Citation Number: 27

Abstract

The Sommelet-Hauser rearrangement is well known as a regioselective rearrangement of benzyldialkylammonium N-methylides to give ortho-substituted benzylamine derivatives.'Hauser et reported that this rearrangement is also applicable to a ring expansion reaction giving cyclic amines. For example, 2-methy1-2, 3, 4, 5, 6, 7-hexahydro-lH-2- benzazonine (6a) and its analogues (6b and 6c) were prepared in high yields by the ylide ...