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化学学报
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化学学报 ›› 1961, Vol. 27 ›› Issue (2): 113-118. 上一篇    下一篇

硫醇对炔属化合物的加成反应的研究 Ⅰ.苯硫酚与苯乙炔的加成反应

刘有成, 王序昆   

  1. 兰州大学化学系
  • 投稿日期:1960-05-30 发布日期:2013-06-03

STUDIES ON THE ADDITION OF THIOLS ON ACETYLENIC COMPOUNDS Ⅰ. THE ADDITION REACTION BETWEEN THIOPHENOL AND PHENYLACETYLENE

LIU YU-CHENG, WANG SUE-KWUNG   

  1. Department of Chemistry, Lanchow University
  • Received:1960-05-30 Published:2013-06-03

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苯硫酚与苯乙炔在0°和室温下进行加成反应时生成反式β-苯硫基苯乙烯,在-20°或-40°时加成则生成约等量的反式和顺式β-苯硫基苯乙烯.顺式β-苯硫基苯乙烯在加热至180°时变化为其反式异构体.苯硫酚的钠盐与苯乙炔在无水乙醇中起加成时则只生成顺式β-苯硫基苯乙烯.苯硫酚对苯乙炔的直接加成可能按自由基链式历程进行,加成反应的立体化学与中间生成的自由基C6H5C=CHSC6H5在反应温度下的稳定性有关,在低温下反式加成较为有利.文中述及顺式和反式β-苯硫基苯乙烯及其砜的紫外吸收光谱.

The addition reaction between thiophenol and phenylacetylene has been studied.With molar ratio of 1:1 the two reactants add rapidly at 00, giving traps-f3-phenylmercaptostyrene in quantitative yield.When the addition reaction was conducted at -20° or -40°, the adducts consisted of about equal amounts of trans- and cis-β-phenylmercaptostyrene.The cis-β-phenylmercaptostyrene was converted to the traps isomer upon heating to 180°.Sodium thiophenolate added on phenylacetylene in absolute alcohol yielded cis-β-phenylmercaptostyrene as the sole product.