The photochemistry of acyl azides - IX. Direct and sensitized photolytic generation of acylnitrenes for cycloaddition reactions

Article abstract of DOI:10.1016/0040-4020(95)00366-G

Contrary to ethoxycarbonylnitrene, selective reactions - including cycloadditions - can be carried out with benzoylnitrene. This study analyzes the sequence of reactivity of various bond types with respect to benzoylnitrene, which was generated by three different routes: direct photolysis of benzoyl azide, sensitization of azide decomposition via energy transfer, and photoinduced electron transfer. In all cases the same cycloadducts 23, 24, and 30 were obtained. Carbonyl activity determines the reactivity of unsaturated ketones and aldehydes with respect to benzoylnitrene.