有机化学 ›› 1998, Vol. 18 ›› Issue (5): 473-477. 上一篇    下一篇

研究论文

β-砜基醇衍生物还原中的基团效应

靳立人   

  1. 厦门大学化学系.厦门(361005)
  • 发布日期:1998-10-25

Effects of functional groups on the reduction of β-sulfonyl alcohol derivatives

Jin Liren   

  1. Xiamen Univ, Dept Chem.Xiamen(361005)
  • Published:1998-10-25

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。

关键词: 烯烃络合物, 砜, 反应机理, 钠汞齐, 单电子转移反应, 中国科学院金属有机化学实验室资助基金, 基团效应, 汞齐还原, 砜基醇

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

Key words: SULFONE, REACTION MECHANISM, SINGLE ELECTRON TRANSFER REACTION, SODIUM AMALGAM, AMALGAM REDUCTION, AKENE COMPLEX

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