Studies in Mass Spectrometry. I. Structures and Reactions of Ions from Benzyl Alcohol, ortho-, meta-, and para-Hydroxybenzyl Alcohols, and their 0-Deuterated Derivatives

Abstract

The work described in the present paper, which was undertaken in the course of investigations into the mass spectra of coal and coal fractions, led the author to propose mechanisms of dissociation and rearrangement reactions of ions derived from benzyl alcohol and from o-, m-, and p-hydroxybenzyl alcohol on the basis of a study of;

(i) the mass spectra of these latter compounds, including comparable features in the mass spectra of 1,4-cyclohexadiene and O-deuterated o- and p-cresols;

(ii) the mass spectra of the corresponding 0-deuterated benzyl and hydroxybenzyl alcohols;

(iii) meta-stable transitions.

π-Complex structures may play an important role in the dissociation of some of the ions-for example, in the loss of D₂O from molecular ions of m- and p-hydroxybenzyl alcohols.