高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (4): 727.

• 研究论文 • 上一篇    下一篇

官能化二硫缩烯酮的选择性α-溴代反应

巴哈尔古丽·别克吐尔逊1,2, 王芒1, 韩锋1, 刘群1   

  1. 1. 东北师范大学化学学院, 长春 130024;
    2. 伊犁师范学院化学系, 伊犁 835000
  • 收稿日期:2009-05-12 出版日期:2010-04-10 发布日期:2010-04-10
  • 通讯作者: 王芒, 女, 博士, 副教授, 主要从事有机合成研究. E-mail: wangm452@nenu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 20872015)和东北师范大学分析测试基金(2009)资助.

Selective α-Bromination of Functionalized Ketene Dithioacetals

BEKTURHUM Bahargul1,2, WANG Mang1*, HAN Feng1, LIU Qun1   

  1. 1. Faculty of Chemistry, Northeast Normal University, Changchun 130024, China;
    2. Department of Chemistry, Yili Normal University, Yili 835000, China
  • Received:2009-05-12 Online:2010-04-10 Published:2010-04-10
  • Contact: WANG Mang. E-mail: wangm452@nenu.edu.cn
  • Supported by:

    国家自然科学基金(批准号: 20872015)和东北师范大学分析测试基金(2009)资助.

摘要:

发展了一种适用范围广、高效且高选择性的官能化二硫缩烯酮的α-溴代反应. 在少量水存在下, 在四氢呋喃溶液中, 以溴化铜为溴代试剂, 经由官能化二硫缩烯酮(1)的α-溴代反应制备了结构多样的α-溴代二硫缩烯酮(2).

关键词: 官能化二硫缩烯酮; 溴化铜; α-溴代反应

Abstract:

Functionalized ketene dithioacetals are important intermediates in organic synthesis. α-Functiona-lization reactions based on them provide potential precursors for the construction of usefully carbo- and heterocyclic compounds. In this paper, a versatile α-bromination of functionalized ketene dithioacetals was developed. In the presence of H2O, the reactions of functionalized ketene dithioacetals(1) with CuBr2 in THF at room temperature gave various α-bromo ketene dithioacetals(2) in excellent yields with high regioselectivities. The mechanism of this α-bromination is proposed to undergo an addition of bromine formed in situ to compound 1 and sequontial elimination of the α-proton. The simplicity of execution, mild conditions, inexpensive, easily usable brominating agent and high yields, make this synthetic method attractive for practical applications.

Key words: Functionalized ketene dithioacetal; Cupric bromide; α-Bromination

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