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1,3-Oxathiolan-Synthese: Spirocyclische 1,3-Oxathiolane aus der Lewis-Säure-katalysierten Umsetzung von cyclischen Trithiocarbonaten und Oxiranen


Oremus, Vladimir; Linden, Anthony; Heimgartner, Heinz (1991). 1,3-Oxathiolan-Synthese: Spirocyclische 1,3-Oxathiolane aus der Lewis-Säure-katalysierten Umsetzung von cyclischen Trithiocarbonaten und Oxiranen. Helvetica Chimica Acta, 74(7):1500-1510.

Abstract

The cyclic trithiocarbonates 1,3-dithioIane-2-thione (4) and 1,3-dithiole-2-thione (9) in 1,2-dichloroethane and MeCN, respectively, react with alkyl- and phenyl-substituted oxiranes 2 in the presence of Lewis acids to give 1-oxa-4,6,9-trithiaspiro[4.4]nonanes 5 and 6 (Scheme 2) and 1-oxa-4,6,9-trithiaspiro[4.4]non-7-enes 10 and 11 (Scheme 3), respectively. The reactions proceed regioselectively yielding 2-alky1 (5,10) and 3-phenyl derivatives (6, 11) as the main products. From the reaction of 4 and 2-phenyloxirane (2e) with TiCl4, 2-phenyl-1,4,6,9-tetrathiaspiro[4.4]nonane (7) is isolated as a minor product. The molecular structures of 5a, 6e, and 7 are established by X-ray crystallography.

Abstract

The cyclic trithiocarbonates 1,3-dithioIane-2-thione (4) and 1,3-dithiole-2-thione (9) in 1,2-dichloroethane and MeCN, respectively, react with alkyl- and phenyl-substituted oxiranes 2 in the presence of Lewis acids to give 1-oxa-4,6,9-trithiaspiro[4.4]nonanes 5 and 6 (Scheme 2) and 1-oxa-4,6,9-trithiaspiro[4.4]non-7-enes 10 and 11 (Scheme 3), respectively. The reactions proceed regioselectively yielding 2-alky1 (5,10) and 3-phenyl derivatives (6, 11) as the main products. From the reaction of 4 and 2-phenyloxirane (2e) with TiCl4, 2-phenyl-1,4,6,9-tetrathiaspiro[4.4]nonane (7) is isolated as a minor product. The molecular structures of 5a, 6e, and 7 are established by X-ray crystallography.

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Additional indexing

Other titles:1,3-Oxathiolane Synthesis: Spirocyclic 1,3-Oxathiolanes from the Lewis-Acid-Catalyzed Reaction of Cyclic Trithiocarbonates and Oxiranes
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1991
Deposited On:13 Mar 2014 08:07
Last Modified:07 Dec 2017 08:22
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19910740714

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