Reactions of iodine(I) azide with αβ-unsaturated carbonyl compounds

Abstract

The addition of iodine(I) azide to some αβ-unsaturated esters and ketones has been examined. Addition to the esters under nitrogen gives products consistent with a radical pathway. Preliminary kinetic results indicate that addition of iodine(I) azide to αβ-unsaturated ketones in the presence of air involves a slow electrophilic attack. Reaction with methyl trans-cinnamate under these conditions does not go to completion.