.ALPHA.,.BETA.-Epoxy sulfoxides as useful intermediates in Organic synthesis. IX A novel synthesis of alkyl vinyl ketones and divinyl ketones from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide as a three-carbon homologating agent.

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The α,β-epoxy sulfoxides easily derived from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide were treated with sodium benzeneselenolate to give β-phenylthio carbonyl compounds in excellent yields. The phenylthio group was oxidized to the sulfinyl group and was then treated with a base to afford alkyl vinyl ketones in quite good yields. This reaction presents a novel method for the preparation of alkyl vinyl ketones from carbonyl compounds by three-carbon homologation. The treatment of α,β-epoxy sulfoxides mentioned above with benzenethiolate gave α,β′-bis(phenylthio) ketones. The elimination of the both thio groups afforded divinyl ketones.
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