Regio- and Stereoselective Formation of 1,3-Oxathiolanes by Reactions of Thiocarbonyl Compounds with Oxiranes

Lewis acid-catalyzed reactions of oxiranes with a variety of C═S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction p...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2005-05, Vol.180 (5-6), p.1309-1313
Main Authors: Heimgartner, Heinz, Fu, Changchun, Blagoev, Milen, Linden, Anthony
Format: Article
Language:English
Subjects:
1,3-Oxathiolanes
oxiranes
ring enlargement
stereoselectivity
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Summary:Lewis acid-catalyzed reactions of oxiranes with a variety of C═S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-atom. The formation of thiocarbonylium ions as intermediates is supported by Wagner-Meerwein-type rearrangements. Enolized thioketones react with oxiranes to give enesulfanyl alcohols, which undergo an acid-catalyzed cyclization to yield 1,3-oxathiolanes.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500590912240