Skeletal rearrangement of α-hydroxy-ketones upon electron impact

Abstract

A skeletal rearrangement induced by electron impact in a number of α-hydroxy-ketones has been studied. Methyl, ethyl, and possibly hydrogen undergo ready 1,2-shifts. The rearrangement is not brought about by thermal excitation and is analogous to the acid-catalysed acyloin transformation described by Favorskii. Evidence is presented that the electron-impact induced transformation proceeds by rearrangement of the molecular ions, and the possibility of determining migratory aptitudes is discussed.