Synthesis of Thione-Propiolic Acid Adducts |
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Authors: | Kentaro Okuma Shinobu Maekawa |
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Affiliation: | Department of Chemistry, Faculty of Science , Fukuoka University , Fukuoka, Japan |
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Abstract: | Abstract Reaction of adamantane-2-thione with propiolic acid gave a novel type of cycloadducts, spiro[adamantane-2,2′-(1,3)-oxathiin]6-one, quantitatively. Thiocamphor and thiofenchone also reacted with propiolic acid to give the corresponding adducts stereoselectively. The observation of second-order reaction kinetics and highly stereoselective addition strongly support a cycloaddition mechanism for the thermal addition. The reaction of selenoketones with propiolic acid afforded a similar cylcoadduct. This is the first example of the reaction of monomeric thiones or selones with acetylenic acids. |
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Keywords: | Cycloaddition propiolic acid selone thiodioxenone thione |
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