Do carbanions undergo 1,2 hydrogen transfers in the gas phase?

Abstract

Certain anions X–⁻CH–CH₂–Y and X–CH₂⁻CH–Y interconvert under collisional activation conditions in the gas phase. Experiments designed to probe the mechanism(s) of particular interconversions suggest (i) that the ions MeO–CH₂–⁻CH–CN and MeO–⁻CH–CH₂–CN interconvert via 1,2 H transfer processes, and (ii) when X = Ph and Y = CO₂Me or CN, deuterium labelling and fragmentation data indicate that equilibration of Ph–⁻CHCH₂Y and PhCH₂–⁻CHY occurs, at least in part, by proton transfer to and from the phenyl ring.