Transannular reactions of 5-hydroxylamino and 5-azido dibenzo[a,e]cyclo-octatrienes: regiospecific syntheses of dibenzohomotropane and pavine analogues
Abstract
5-Hydroxylamino- and 5-methoxylamino-5-methyldibenzo[a,e]cyclo-octatrienes readily cyclise to give azabicyclo[4.2.1]nonane (dibenzohomotropane) products; thermolysis of the 5-azide yields the tricyclic [3.2.1.0] aziridine, which selectively cleaves to give the azabicyclo[3.3.1]nonane (pavine) ring system.