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Abstract 1‐Alkynyl sulfides R 1 C≡C‐S‐R 2 1 are easily converted with a copper(I) hydride complex in tetrahydrofuran into cis ‐1‐alkenyl sulfides R 1 CHCH‐S‐R 2 2 in yields >90%. Treatment of compounds 1 with LiAlH 4 in the same solvent leads to the isomeric trans ‐1‐alkenyl sulfides R 1 CH CH‐S‐R 2 3 in almost quantitative yield.
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Vermeer et al. (1976) studied this question.
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