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Original Articles

Synthesis of Thione-Propiolic Acid Adducts

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Pages 1357-1361 | Received 09 Jul 2004, Accepted 05 Oct 2004, Published online: 16 Aug 2006
 

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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