β-砜基醇衍生物还原中的基团效应

Effects of Functional Groups on the Reduction of P-Sulfonyl Alcohol Drivatives

比较芳香族砜基和脂肪族砜基对钠-汞齐还原β-砜基醇衍生物反应的影响。在还原β-苯基砜基醇衍生物的反应条件下,β-叔丁基砜基醇衍生物并不能得到还原去砜基的烯烃。β-苯基砜基醇衍生物可能是经过单电子转移消除的机理,而β-叔丁基砜基醇甲磺酰化物则经α-砜基碳负离子的消除过程得到烯烃基砜。

Effects of phenylsulfonyl and t - butylsulfonyl on the reduction of P - sulfonyl alcohol derivatives with Na - Hg were compared. B - t - butylsulfonyl alcohol derivatives was not reduced to alkene under the same conditions as reduction of 3 - phenylsulfonyl alcohol derivatives with Na - Hg . B - Phenylsulfonyl alcohol derivatives were reduced probably via single electron transfer elimination, and B - t - butylsulfonyl alcohol mesylate underwent elimination via a - sulfonylcarbanion to give the alkenyl sulfone.