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Issue 0, 1981
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Reduction of β-arylthio- or β-alkylthio-αβ-unsaturated ketones

Abstract

The preparation and reduction of β-arylthio- or β-alkylthio-αβ-unsaturated ketones (1) with lithium aluminium hydride or sodium borohydride have been examined. Reduction of the ketones (1) with lithium aluminium hydride gave αβ-unsaturated ketones (2), in which the olefinic (R1) and carbonyl (R2) substituents are reversed compared with the starting αβ-unsaturated ketone (1), or the saturated γ-hydroxy-sulphides (3). Reduction of the ketones (1) with sodium borohydride afforded only the αβ-unsaturated ketones (2). Reduction of (1) with sodium borohydride in the presence of metal halides gave the saturated ketones (5).

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Article information


J. Chem. Soc., Perkin Trans. 1, 1981, 934-938
Article type
Paper

Reduction of β-arylthio- or β-alkylthio-αβ-unsaturated ketones

T. Nishio and Y. Omote, J. Chem. Soc., Perkin Trans. 1, 1981, 934
DOI: 10.1039/P19810000934

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