A Novel Synthesis of α,α-Dicarbonyl andα-Oxo-α-alkoxide Cyclic O,S-Ethylene Acetales

Abstract

Abstract: Anew method for the synthesis of the tit1e compounds 6 is described in this paper.Compounds 6 were obtained by an one-pot reaction process from β-dione and its analogues, 2-bromoethanol and carbon disulfide with potassium carbonate as the base.The possible mechanism is discussed.In this mechanism, a monoanion intermediate 3 is proposed, it reacts with 2-bromoethanol by a sequential nucleophilic and electrophilic reaction process to build the key intermediate 5.6 is formed by the elimination of hydrosulfide from 5.

Key words: α-Oxo ketene cyclic O, S-ethylene acetals, Synthesis, α-Oxo ketene dithioacetals, 2-Bromoethanol

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ZHANG Shu-Jia, LIU Qun, XIE Zhong-Wei, QIU Xue-Fei, Dilifeiger, ZHANG Qian, LIU Jing-Fu. A Novel Synthesis of α,α-Dicarbonyl andα-Oxo-α-alkoxide Cyclic O,S-Ethylene Acetales[J]. Chem. J. Chinese Universities, 1997, 18(2): 257.

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A Novel Synthesis of α,α-Dicarbonyl andα-Oxo-α-alkoxide Cyclic O,S-Ethylene Acetales

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