Synthesis and R eactions of Some 2,2-Disubstitued 1,2-Diazetidin-3-ones: An Intramolecular Aldol Approach to Bicyclic Systems

Article abstract of DOI:10.1021/jo00359a028

Several procedures have been developed for alkylation at N-2 of a variety of 1,2-diazetidin-3-ones with N-1 substituent carrying an olefinic bond.Ozonolysis yielded aldehydes which were subjected to aldol cyclization conditions.The products proved to be rearranged bicyclic products arising from intramolecular ring opening of the 1,2-diazetidin-3-one lactam bond by the secondary hydroxyl group formed in the aldol reaction.