Acetone chemical ionization studies III-displacement reactions in alkyl acetates

Abstract

Acetone chemical ionization mass spectra of acyclic, cyclic and bicyclic alkyl acetates were studied. In addition to the formation of [M + H]⁺, [M + 43]⁺ and [M + 59]⁺ ions, ions corresponding to displacement by acetone were also observed. The results suggest that the displacement by acetone follows an S_N1-like mechanism in the source of the mass spectrometer. Similarity between solution-phase solvolysis reactions and gas-phase displacement reactions was observed with bicyclic alkyl acetates, 2-phenylethyl acetate and cyclooctyl acetate.