Journal of the Chemical Society. Perkin transactions I p. 934 - 938 (1981)
Update date:2022-07-29
Topics:
Nishio, Takehiko
Omote, Yoshimori
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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