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26.1.1.2.5 Method 5: Oxidation of Secondary Alcohols with Halogen Compounds

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052660.

Halogens in a positive oxidation state are appropriate agents for the oxidation of secondary alcohols to ketones with the exception of fluorine, which does not form such compounds. However, molecular fluorine can react with water in the presence of acetonitrile to give a reagent which formally resembles hypochlorite but the polarity of the halogen and oxygen is reversed.[‌148‌] Organic derivatives of chlorine, e.g. substituted imidoyl derivatives, and iodine, e.g. iodosylbenzene and periodinane, have found wider applications. In the presence of additives the elemental halogens chlorine,[‌149‌] bromine,[‌149‌] and iodine[‌150‌] can be used as oxidants for the conversion of secondary alcohols into ketones.

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