Oxidative displacement of hypervalent iodine from alkyl iodides

Abstract

Oxidative displacement of iodine from primary alkyl iodides and vic-substituted iodocyclohexanes with m-chloroperbenzoic acid in either dichloromethane or t-butyl alcohol–water gives primary alcohols and vic-substituted cyclohexanols, respectively. Retention of configuration at the displacement centre occurs for all of the trans-vic-substituted iodocyclohexanes except the iodoacetate and iodotrifluoroacetate where inversion of configuration occurs to give cis-hydroxy-esters. Oxidation of (S)-2-iodo-octane occurs with almost complete inversion to give (R)-octan-2-ol but also affords octan-1-ol, octan-3-ol, and octan-2-one.