Evidence for the formation of exo and endo aziridines in the reaction of cis–endo and cis–exo-bicyclo[2•2•1]-5-heptene-2,3-dicarboxylic anhydride and benzenesulfonyl azide

Abstract

Benzenesulfonyl azide has been found to react with cis–endo and cis–exo bicyclo[2•2•1]-5-heptene-2,3-dicarboxylic anhydride to give in both cases, predominantly the more hindered endo aziridine in addition to the exo aziridine in apparent violation of the "exo-addition rule" (3). The stereochemistry of the aziridine rings were determined by nuclear magnetic resonance analysis and by conversion of the endo-aziridine-exo-anhydride to 2-endo-benzenesulfonamidobicyclo[2•2•1]heptane. The endo-aziridine-endo-anhydride has been previously (4) converted into a lactone-N-benzenesulfonyl-lactam.