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Chemo- and regiospecific monoaddition of secondary phosphine sulfides to 1-acyl-2-phenylacetylenes

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TAYLOR & FRANCIS LTD
DOI: 10.1080/10426500701648069

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1-acyl-2-phenylacetylenes; 3-(diphenethylphosphorothioyl)-1-R-3-phenyl-2-propen-1-one; bis(2-phenylethyl) phosphine sulfide; nucleophilic monoaddition

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Secondary phosphine sulfides react with 1-acyl-2-phenylacetylenes under mild conditions (KOH, THF, r.t.) to afford chemo-and regiospecifically 3-diorganophosphorothioyl-1-R-3-phenyl-2-propen-1-ones in high yield, with the E-isomers being formed exclusively (R = Ph and 2-thienyl) or predominantly (60%, R = Me).

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