1351865-58-1Relevant articles and documents
The bromodiazirinyl anion: A weakly bound complex of diazirinylidene and a bromide ion
Martinu, Tomas,Boehm, Stanislav,Hanzlova, Eva
, p. 6254 - 6260 (2011/12/15)
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-CN2 (diazirinylidene) and a bromide ion. We explain the formation of substantial amounts of di-n-butoxymethane in the presence of n-butanol by a sequence of O-H insertion and denitrogenation reactions of the putative c-CN2 carbene. This ground-state singlet species is the last undescribed member of the CN2 family of reactive intermediates. It differs from classical N-heterocyclic carbenes by its high ionization potential and electron affinity.
