Beckmann rearrangement of 1,2,3,8-tetrahydro-1-hydroxyiminocyclopent[a]indene and 1,2,3,4-tetrahydro-1-hydroxyiminofluorene

Abstract

Beckmann rearrangement of 1,2,3,8-tetrahydro-1-hydroxyiminocyclopent[a]indene and 1,2,3,4-tetrahydro-1-hydroxyiminofluorene under a variety of conditions, and also Schmidt rearrangement of the parent ketones, gave solely the products of alkyl migration, 3,4-dihydro-9H-indeno[2,1-c]pyridin-1 (2H)-one and 3,4,5,10-tetrahydroindeno[2,1-c]azepin-1(2H)-one respectively. It is suggested that the rearrangements occur via a non-stereo-selective iminium cation.