Aspects of the addition of iodine(I) azide to alkenes

Abstract

Iodine(I) azide, formed from sodium azide–iodine(I) chloride, exists in acetonitrile as a complex with sodium azide. Addition of iodine(I) azide to cyclohexene gives a cis-iodo-azide as well as the expected trans-adduct. The addition of iodine(I) azide to a mixture of (Z)- and (E)-[β-²H]styrene occurs in a stereospecific manner. In contrast to a literature report, the addition of iodine(I) azide to 1-methylcyclohexene is faster than to cyclohexene. Intermediates in these reactions are discussed.