The thermal rearrangement of 1-substituted 1H-azepines to 6-amino-fulvenes

Abstract

Thermal rearrangements of 6,7,8,9-tetrahydro-2,4-dimethyl-3H-3-benzazepine-1,5-dicarbonitrile (XVI) yields 4,5,6,7-tetrahydro-1-(1-methyliminoethyl)-2-methylindene-1,3-dicarbonitrile (XVIII; R = :NMe). Compounds of the latter type are considered to be intermediates in the thermal rearrangement of 1-substituted 1H-azepines to fulvenes, where a subsequent [1,5] sigmatropic rearrangement of the imine group is also involved.