Acta Chimica Sinica ›› 1965, Vol. 31 ›› Issue (6): 451-457.     Next Articles

硫醇对炔属化合物的加成反应 Ⅴ.苯硫酚对几种炔烃加成的立体化学

刘有成, 王序昆   

  1. 兰州大学化学系
  • 投稿日期:1963-10-04 修回日期:1965-06-03 发布日期:2013-06-03

STUDIES ON THE ADDITION OF THIOLS TO ACETYLENIC COMPOUNDS Ⅴ. THE STEREOCHEMISTRY OF THE ADDITION OF THIOPHENOL TO SOME ACETYLENES

LIU Yu-CHENG, WANG SUE-KWUNG   

  1. Department of Chemistry, Lanchow, University
  • Received:1963-10-04 Revised:1965-06-03 Published:2013-06-03

When the direct addition of thiophenol to phenylacetylene, p-bromophenylacetylene,p-nitrophenylacetylene, and propiolic acid was conducted at room temperature, the corresponding 1:1 adducts of traps-configuration were obtained, which were trans-β-phenyl-thiostyrene (Ⅰa),trans-β-phenylthio-p-bromostyrene (Ⅱa),and trans-β-phenylthioacrylic acid (Ⅳa) respectively. The yields of these adducts decreased in the following order:Ⅰa>Ⅱa>Ⅲa>Ⅳa. When the addition of thiophenol to the four acetylenes was carried out in solution at low temperature(-45~-35°),except p-nitrophenylacetylene which did not react under these conditions, all the other three compounds gave adducts only or mostly of cis-configuration (traps addition),which were cis-β-phenylthiostyrene (Ⅰb, 100%) cis-phenylthio-p-bromostyrene(Ⅱb, 75%) and cis-phenylthioacrylic acid (Ⅳb, 80%). All these compounds of cis-configuration were stable under the reaction conditions, being transformed to trans-configuration only on heating to or above 160°.