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Synthesis of 4,4-Diethylthio/benzylthio-but-3-en-2-one and Application as Odorless Thiol Equivalents in Thioacetalization

YU Hai-Feng1,2, WANG Yan-Ru3, OUYANG Yan1, WANG Yan1, LIU Qun1   

    1. Faculty of Chemistry, Northeast Normal University, Changchun 130024, China;
    2. Department of Chemistry, Anshan Teachers College, Anshan 114005, China;
    3. Public Foundation Department of Beihua University, Jilin 132013, China
  • Received:2005-11-14 Revised:1900-01-01 Online:2006-12-10 Published:2006-12-10
  • Contact: LIU Qun

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Abstract: 4,4-Diethylthio/benzylthio-but-3-en-2-ones 2 were prepared in excellent yields by the acid-catalyzed deacetylation of 3-(diethylthio/benzylthio)methylene-pentane-2,4-diones(1). With ketene diethylthio/benzylthioacetals(2) as the odorless thiol equivalents, in the presence of acetyl chloride, a series of diethylthio-/dibenzylthioacetals were prepared via the reaction of compound 2 with aldehydes/ketones in methanol under mild conditions.

Key words: α-Oxo ketene-S,S-acetals, 4,4-Bis(ethylthio/benzylthio)but-3-en-2-ones, Odorless thiol equi-valents, Thioacetalization

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