Reduction of β-arylthio- or β-alkylthio-αβ-unsaturated ketones
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 934-938
- https://doi.org/10.1039/p19810000934
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).Keywords
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