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Issue 14, 2006
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Reaction of thioketones with propiolic acids

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The reaction of adamantane-2-thione with propiolic acid afforded a novel type of cycloadduct, spiro[adamantane-2,2′-6′H-[1,3]-oxathiin]-6′-one (3a), in quantitative yield. The reaction of thiobenzophenone with propiolic acid gave 2,2-diphenyl-6′H-[1,3]-oxathiin]-6′-one and 4-phenyl-3-thia-3,4-dihydronaphthoic acid in 34% and 35% yields, respectively. The reaction might proceed through a concerted process, as confirmed by kinetics. The reaction of adamantane-2-thione with 2-butynoic acid or phenylpropiolic acid gave the corresponding adducts regioselectively. Interestingly, only one isomer was obtained by the reaction of thiofenchone with propiolic acid, suggesting that the reaction proceeded diastereospecifically. Oxidation of adducts 3 by dimethyldioxirane or m-chloroperoxybenzoic acid gave the corresponding sulfoxides and sulfones. The sulfoxides were thermally decomposed to give disulfide or another type of 1,3-oxathiin-6-one.

Graphical abstract: Reaction of thioketones with propiolic acids

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The article was received on 07 Apr 2006, accepted on 24 May 2006 and first published on 12 Jun 2006

Article type: Paper
DOI: 10.1039/B605068A
Citation: Org. Biomol. Chem., 2006,4, 2745-2752
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    Reaction of thioketones with propiolic acids

    K. Okuma, M. Koda, S. Maekawa, K. Shioji, T. Inoue, T. Kurisaki, H. Wakita and Y. Yokomori, Org. Biomol. Chem., 2006, 4, 2745
    DOI: 10.1039/B605068A

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