高等学校化学学报 ›› 2006, Vol. 27 ›› Issue (3): 482.

• 研究简报 • 上一篇    下一篇

α-乙酰基二硫缩烯酮的新合成方法

赵玉龙1,刘群1,张薇1,于海丰1,2,刘郁1,林春2   

  1. 1. 东北师范大学化学学院,长春130024; 2. 鞍山师范学院化学系,鞍山 114005
  • 收稿日期:2005-03-11 出版日期:2006-03-10 发布日期:2006-03-10
  • 通讯作者: 刘群(1955年出生),男,教授,博士生导师,从事有机合成化学研究. E-mail: liuqun@nenu.edu.cn

A New Method for the Synthesis of α-Acetyl Ketene Dithioacetals

ZHAO Yu-Long1,LIU Qun1*,ZHANG Wei1,YU Hai-Feng1,2,LIU Yu1,LIN Chun2   

  1. 1. Falculty of Chemistry,Northeast Normal University,Changchun 130024,China;
    2. Department of Chemistry,Anshan Normal College,Anshan 114005,China
  • Received:2005-03-11 Online:2006-03-10 Published:2006-03-10

摘要:

本文采用酸为催化剂,实施了具有代表性的各种烷硫基α,α-二乙酰基二硫缩烯酮的脱乙酰基反应,得到了一条简洁、通用的α-乙酰基二硫缩烯酮的合成路线.用浓硫酸作催化剂,以极高的产率(90%—100%)制得到相应的α-乙酰基二硫缩烯酮.同时,通过控制反应时间,还可以得到硫代乙酰乙酸酯类化合物.

关键词: α,α-二乙酰基二硫缩烯酮; 浓硫酸; 脱乙酰基; α-乙酰基二硫缩烯酮; 硫代乙酰乙酸酯

Abstract:

The α-acetyl ketene dithioacetals 2,which bear various alkylthio groups,are a kind of important intermediates in organic synthesis. In this paper,dithioacetals 2 were prepared in very high yields (90%—100%) via the deacetylation reaction of the corresponding α,α-diacetyl ketene dithioacetals 1 in the presence of concentrated sulfuric acid. This reaction involves an in-situ electrophilic addition-deacetylation mechanism and shows the nucleophilicity of the α-carbon atom in α-oxo ketenedithioacetals. Meanwhile,when the reaction time was prolonged to 22—25 h,the β-keto thiolesters 3a and 3c were produced in good yields.

Key words: α,α-Diacetyl ketene dithioacetals; Concentrated sulfuric acid; Deacetylation; α-Acetyl ketene dithioacetals; β-Keto thiolesters

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