Addition of iodine(I) azide to 3-t-butylcyclohexene and 3-methoxycyclohexene

Abstract

Iodo-azides have been prepared from 3-t-butylcyclohexene and 3-methoxycyclohexene. In each case the major product can be rationalised as that arising by antiparallel opening of a cis-iodonium ion to give a trans-diaxial adduct, and the minor product as that arising by parallel opening of a trans-iodonium ion to give a trans-diequatorial adduct. However, the major product from 3-methoxycyclohexene undergoes a conformational inversion to give a trans-diequatorial adduct. The ratio of products derived from cis- and trans-iodonium ions varies with the iodoazide producing system and is larger for 3-methoxycyclohexene, especially when dichloromethane is the solvent. Solvolysis of the products has been investigated.