Reactions of 4,8-dimethylbicyclo[3.3.1]nona-3,7-diene-2,6-dione and of 4,6-dimethylbicyclo[3.3.1]nona-3,6-diene-2,8-dione with hydroxylamine and with hydrazines

Abstract

Hydrazine reacts with 4,8-dimethylbicyclo[3.3.1]nona-3,7-diene-2,6-dione by condensation and Michael-type addition to give 4,9-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.^4,120^6,10]trideca-1,6-diene, but hydroxylamine and other hydrazine derivatives only give bicyclic condensation products. Beckmann rearrangement of the oximes of 4,8-dimethylbicyclo[3.3.1]nona-3,7-diene-2,6-dione and of 4,6-dimethylbicyclo[3.3.1]nona-3,6-diene-2,8-dione gives 2-azabicyclo[4.3.1]decadienediones.