The oxidation of secondary and tertiary alcohols by nitrous acid
Abstract
The oxidation of 2-phenylpropan-2-ol to acetophenone by nitrous acid in aqueous sulphuric acid takes place following rate-determining dehydration to α-methylstyrene, and the nitrous acid oxidation of 1-arylethanols consists of two competing reactions which are α-hydride abstraction by nitrosonium ion to give the acetophenone and dehydration followed by oxidation of the styrene to give the benzaldehyde.