Internal addition of acyl nitrenes to olefins

Abstract

Photolysis of cycloheptene-5-carbonyl azide, endo-norbornene-5-carbonyl azide and o-vinylbenzoyl azide gave very reactive acyl aziridines by internal addition of acyl nitrenes to the olefinic double bonds. Derivatives of 6-azabicyclo-[3,2,2]nonane and 1,2-dihydroisoindol-1-one were prepared. cis-2-Vinyl-cyclopropyl isocyanate, prepared photochemically at −78°, underwent Cope rearrangement at room temperature to 2,3-dihydro-1H-azepin-2-one. The mass spectra of a series of lactams are interpreted.