Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (4): 727.

• Articles • Previous Articles     Next Articles

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.

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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