title: Type 1 Ring-Opening Reactions of Cyclopropanated 7-Azabenzonorbornadienes with Organocuprates.
abstract: The first nucleophilic ring-opening reactions of cyclopropanated 7-azabenzonorbornadienes have been achieved using organocuprates. Tricyclic or tetracyclic γ-lactams were obtained as the sole product in good yields of up to 98% when alkoxycarbonyl groups occupied the N-substituent position. Successful conversions to lactams were observed for primary, secondary, tertiary, and aromatic nucleophiles, as well as for a variety of substrates functionalized on the benzene ring. A possible mechanism for these transformations is discussed.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph , Guelph, Ontario N1G 2W1, Canada.
authors.forename: Emily
authors.initials: E
authors.lastname: Carlson
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph , Guelph, Ontario N1G 2W1, Canada.
authors.forename: William
authors.initials: W
authors.lastname: Tam