Benzoylnitrene radical anion: a new reagent for the generation of M-2H anions.

Benzoylnitrene radical anion, formed in high abundance by electron ionization of benzoylazide, is found to be a useful reagent for the formation of ionized reactive intermediates, such as diradicals and carbenes. The reactivity of the ion is similar to what is observed with atomic oxygen anion, occurring in many instances by H(2)(+) transfer. However, because benzoylnitrene radical anion is less basic than oxygen anion, it undergoes H(2)(+) transfer with substrates that react with oxygen anion by only proton transfer and therefore can be used to generate reactive ions not easily prepared by other methodologies.