Experimental and computational evidence will be presented that 3-halodiazirinyl anions should be regarded as complexes of diazirinylidene and halide ions, closely paralleling the known equilibrium between trihalomethyl anions and dihalomethylenes. 3-Bromo-3-carboalkoxy-3H-diazirines undergo facile nucleophilic acyl displacement of 3-bromodiazirinyl anion, which exhibits carbenic reactivity, e.g., insertion into an O-H bond. The ground-state singlet diazirinylidene has been calculated to possess electron affinity similar to that of chlorofluorocarbene, and ionization potential higher than that of difluorocarbene.

3-Halodiazirinyl anion: A complex of diazirinylidene and halide ion

240th National Meeting (2010)

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