α-乙酰基二硫缩烯酮的新合成方法  

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

作　　者：赵玉龙[1] 刘群[1] 张薇[1] 于海丰[1] 刘郁[1] 林春[2] 

机构地区：[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

出　　处：《高等学校化学学报》2006年第3期482-484,共3页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20272008);教育部科学技术研究重大项目资金(批准号:10412)资助.

摘　　要：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.The α-acetyl ketene dithioacetals 2, which bear various alkyhhio 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.

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 

分 类 号：O629[理学—有机化学]