N-heterocyclization in electrophilic haloamidation reactions of 1, 5-cyclooctadiene: synthesis and rearrangements of the granatanine and homonortropane skeletons

9-azabicyclononanes 2 and 3 can be prepared by transannular N-heterocyclization of 1,5-cyclooctadiene which employs B-bromo- or N-iodosuccinimide and cyanamide. This method is unsuccessful when N-chlorosuccinimide was used. Dehydration of the carboxamide after nucleophilic displacement with chlorine affected the preparation of chloro-substituted derivative.