The free-radical addition of thiophenol to bornylene and apobornylene: structures of product sulphides and sulphones formed on oxidation
作者:D. I. Davies、P. J. Rowley
DOI:10.1039/j39680001832
日期:——
The free-radical addition of thiophenol to bornylene affords phenyl isobornyl sulphide and phenyl epi-isobornyl sulphide, the products of exo radical attack. Oxidation converts these sulphides into the corresponding exo-sulphones, which on treatment with potassium t-butoxide in t-butyl alcohol are epimerized to give the corresponding endo-sulphones, phenyl bornyl sulphone, and phenyl epibornyl sulphone
苯硫酚自由基加到冰片烯中得到苯异冰片基硫化物和苯表异冰片基硫化物,它们是外自由基攻击的产物。氧化作用将这些硫化物转化为相应的外砜,在叔丁醇中用叔丁醇钾处理后,它们会发生差向异构化,从而生成相应的内砜。-砜,苯基冰片基砜和苯基表冰片基砜。这些结果与将硫醇添加到六氯降冰片二烯上的结果相结合,表明空间效应并不是控制自由基攻击方向的唯一因素。已证明,在首先由波斯纳(Posner)进行的硫酸和乙酸存在下,将苯硫酚加到樟脑中会生成苯基异冰片硫化物。加入苯硫酚apobornylene是类似于除了冰片,和得到的产品外切自由基攻击,苯基异apobornyl硫化物,其在氧化得到相应的外切-sulphone,差向异构化为远藤-sulphone在吨钾存在下丁醇中的叔丁醇。