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Regio- and stereoselective formation of 1,3-Oxathiolanes by reactions of thiocarbonyl compounds with oxiranes


Fu, Changchun; Blagoev, Milen; Linden, Anthony; Heimgartner, Heinz (2005). Regio- and stereoselective formation of 1,3-Oxathiolanes by reactions of thiocarbonyl compounds with oxiranes. Phosphorus, Sulfur and Silicon and the Related Elements, 180(5-6):1309-1313.

Abstract

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.

Abstract

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.

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Additional indexing

Item Type:Journal Article, not refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2005
Deposited On:25 Apr 2013 09:40
Last Modified:23 Nov 2017 17:18
Publisher:Taylor & Francis
ISSN:1026-7719
Additional Information:This is an Author's Accepted Manuscript of an article published in Fu, Changchun; Blagoev, Milen; Linden, Anthony; Heimgartner, Heinz (2005). Regio- and stereoselective formation of 1,3-Oxathiolanes by reactions of thiocarbonyl compounds with oxiranes. Phosphorus, Sulfur and Silicon and the Related Elements, 180(5-6):1309-1313. Copyright Taylor & Francis, available online at: http://www.tandfonline.com/10.1080/10426500590912240.
Publisher DOI:https://doi.org/10.1080/10426500590912240

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