PINACOL REARRANGEMENT OF QUINOLINE ANALOGS OF BENZOPINACOL AND EVIDENCE FOR REARRANGEMENT UNDER CONDITIONS OF ELECTRON IMPACT

The pinacols, 1,2‐di(2‐quinolyl)‐1,2‐diphenylethane‐1,2‐diol and 1,2‐di(8‐quinolyl)‐1,2‐diphenylethane‐1,2‐diol, were prepared and rearranged. The mass spectrum of the phenyl‐2‐quinolylpinacolone showed fragment peaks corresponding to the pinacolone resulting from 2‐quinolyl migration. The mass spectrum of the phenyl‐8‐quinolylpinacolone showed fragment peaks corresponding to the pinacolone resulting from phenyl migration. Evidence for the rearrangement by electron impact was observed in the mass spectrum of each pinacol. Copyright © 1969 Journal of Heterocyclic Chemistry