Oxidative displacement of hypervalent iodine from alkyl iodides
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 822-827
- https://doi.org/10.1039/p19800000822
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.Keywords
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