Synthesis of esters from alcohols or alcohols and aldehydes with t-butyl hypoiodite

Abstract

From studies of the reaction of an aldehyde with an alcohol in the presence of t-butyl hypoiodite (generated from t-butyl hypochlorite, iodine, and potassium t-butoxide), it is proposed that the ester derived from an alcohol and t-butyl hypoiodite in the dark is formed via a polar process in which the intermediate is not the acyl iodide. The acceleration of ester formation when the reaction mixture is irradiated is suggested to be due to hydrogen abstraction from the aldehyde to form the acyl iodide, which then reacts with the alcohol.