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苯硫酚与β-溴苯乙炔在过氧化苯甲酰或紫外光照条件下加成得颇低产率的α-苯基-β-苯硫基溴乙烯,调聚物为主要产品。加成产物用过氧化氢在次醋酸中氧化得-砜“α-苯基-β-苯磺酰基溴乙烯。该砜在乙醇钠-乙醇中消除溴化氢得苯磺酰基苯乙炔,进而证明苯硫基连接到携带溴的碳原子上。该反应按自由基历程进行的,由此可以认为,中间自由基的稳定性是加成方向的决定因素。因为苯基的共轭效应比溴原子大。从本文结果以及其它结果可以排出碳——碳重键上取代基对过渡态的稳定次序:在乙醇钠催化下苯硫酚与β-溴苯乙炔加成得与自由基条件相同的1∶1加成产物。
Thiophenol and β-bromophenylacetylene benzoyl peroxide or under the conditions of the addition of light a very low yield of α-phenyl-β-phenylthio vinyl bromide, telomer as the main product. Adduct with hydrogen peroxide in acetic acid oxidation - sulfone "α-phenyl-β-phenylsulfonyl vinyl bromide. The sulfone in ethanol sodium - ethanol to remove hydrogen bromide to benzenesulfonyl phenylacetylene, which proves The phenylthio group is attached to the carbon atom carrying the bromine.The reaction proceeds according to the radical history whereby it can be assumed that the stability of the intermediate radical is the determining factor for the direction of addition.Because the conjugation of the phenyl group is stronger than that of the bromine atom Large. From this and other results, the order of stability of the transition state on the carbon-carbon multiple bond displacements can be excluded: Addition of thiophenol to β -bromophenylacetylene catalyzed by sodium ethoxide at 1 and the same free radical conditions : 1 Addition products.