Abstract Experimental and computational evidence suggests that the cleavage of n-butyl and tert-butyl 3-bromodiazirine-3-carboxylates by sodium n-butoxide in DMF, affording high yields of dibutyl carbonates, may proceed by nucleophilic acyl displacement of the bromodiazirinyl anion, a weakly bound complex of a cyclic carbene c-CN 2 (diazirinylidene) and a bromide ion. We explain the formation of substantial amounts of di-n- ...
