Synthesis and Reactions of Some 1-Substituted 1,2-Diazetidinones

Article abstract of DOI:10.1021/jo00197a017

A number of 1,2-diazetidin-3-ones variously substituted at N-1 have been prepared by sodium borohydride reduction of, or addition of methylmagnesium bromide to, 3-oxo-1,2-diazetidinium inner salts (formed by condensation of 3-oxo-1,2-diazetidinium tosylate with carbonyl compounds). 1-Cinnamyl-1,2-diazetidin-3-ones, silylated at N-2, underwent base-promoted alkylation and aldol reactions at C-4.Some unusual dimerization and fragmentation reactions of these aza-β-lactam derivatives have been observed.