SOLVOLYSIS OF N-CHLORO-1,4-DIHYDRO-1,4-IMINONAPHTHALENES(7-AZABENZONORBORNADIENES) - DEPENDENCE OF THE REARRANGEMENT PATHWAY ON THE CONFIGURATION AT NITROGEN

N-Chloro- derivatives of the 1,4-dihydro-1,4-iminonaphthalene (7-azabenzonorbonradiene) ring system undergo silver (I)-assisted rearrangement with participation of etheno- (syn-chloro- series) or benzo- (anti-chloro- series) pi-electrons. The high barriers to inversion at nitrogen together with some control over the ratio of invertomers allow observation of a different reaction pathway for each invertomer when reactions are performed at low temperatures; approaches which allow selection of the benzo- participation route (giving 6,7-benzo-derivatives of the 1-azabicyclo[3.2.0]hept-3-ene ring system) are described.