Studies on the Basic Assisted Decomposition of α,α-Dioxo(Ester)Ketene Dithioacetals

Abstract

Abstract: Afacile method for the synthesis of β, β-dialkylthioacrylate is described in this paper. The title compounds 1 prepared easily in nearly quantitive yields from corresponding β-dicarbonyl substrates were decomposed to give compounds 2, assisted by either potassium ethylthioate or sodium(potassium)alkoxide.As shown by the experiments, the former base is very effective, the yields of 2 reach to the range of 66%─98%.The decomposition was proposed to proceed via the Contra-Claisen condensation process in mechanism. This route is common, convenient and is the first example for the synthesis of the compounds 2 with different thioacetal groups in high yields.

Key words: α,α-Dioxo(Ester)ketene dithioacetals, Potassium ethylthiolate, β,β-Dialkylthioacrylate, Decomposition

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ZHANG Shu-Jia, LIU Qun, ZHU Zai-Ming, ZHANG Chang-Shan, HUANG Hui. Studies on the Basic Assisted Decomposition of α,α-Dioxo(Ester)Ketene Dithioacetals[J]. Chem. J. Chinese Universities, 1994, 15(8): 1155.

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Studies on the Basic Assisted Decomposition of α,α-Dioxo(Ester)Ketene Dithioacetals

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