Solutions of carbonyl compounds in dibromodifluoromethane in the presence of hydrogen bromide: protonation of ketones and formation of 1 -bromo-alcohols from aldehydes

Abstract

HBr in CBr₂F₂ is capable of protonating a variety of ketones, and at low temperatures separate ¹H n.m.r. signals can be seen for the acid and protonated base. Line shape analysis of the signals enables rates of protonation to be calculated. Aldehydes in HBr–CBr₂F₂ give n.m.r. spectra that are consistent with the formation of 1-bromoalcohols.