高等学校化学学报

高等学校化学学报

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α-乙酰基二硫缩烯酮α碳原子的酰化反应

尹彦冰1,2, 王岩1, 赵玉龙1, 谭晶1, 刘群1   

    1. 东北师范大学化学学院, 长春 130024;
    2. 齐齐哈尔大学化学化工学院, 齐齐哈尔 161006
  • 收稿日期:2005-12-20 修回日期:1900-01-01 出版日期:2006-12-10 发布日期:2006-12-10
  • 通讯作者: 刘群

Acylation of α-Acetyl Ketendithioacetals with Acyl Chloride

YIN Yan-Bing1,2, WANG Yan1, ZHAO Yu-Long1, TAN Jing1, LIU Qun1   

    1. Falculty of Chemistry, Northeast Normal University, Changchun 130024, China;
    2. Department of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, China
  • Received:2005-12-20 Revised:1900-01-01 Online:2006-12-10 Published:2006-12-10
  • Contact: LIU Qun

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摘要： 进行了α-乙酰基二硫缩烯酮与酰氯的酰化反应. 以干燥的二氯甲烷为溶剂, 在四氯化钛催化下, α-乙酰基环二硫缩烯酮(1)可与脂肪及芳酰氯(2)反应, 在化合物1的α-碳原子上发生酰化反应, 以较高的产率生成各种α-乙酰基-α-酰基二硫缩烯酮(3).

关键词: α-乙酰基二硫缩烯酮, 酰氯, 酰化, α-乙酰基-α-酰基二硫缩烯酮

Abstract: As a kind of versatile synthons, α-oxoketene dithioacetals have found their wide utilizations in organic synthesis. Owing to the interaction between two electron donating groups(RS) and an electron withdrawing group in the α position, the α-carbon atom of α-EWG ketene S,S-acetals shows a high nucleophilicity. In this paper, the reactions of α-acetyl cyclic ketendithioacetals with a series of acyl chlorides were performed and a new route to the C—C bond formation reaction at the α-carbon atom of α-oxoketene dithioacetals was described. By the above reactions, α-acetyl-α-acyl ketendithioacetals were prepared with good to high yields(55%—82%) via the acylation of α-acetyl cyclic ketendithioacetals at the α-carbon atom of α-acetyl ketendithioacetals mediated by titanium tetrachloride in dry dichloromethane at reflux temperature. The mechanism of the acylation between compound 1 and acyl chloride was proposed, which belongs to nucleophilic addition-elimination reaction.

Key words: α-Acetyl ketendithioacetals, Acyl chlorides, Acylation, α-Acetyl-α-acyl ketendithioacetals

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