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.