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.
| Other titles: | 1,3-Oxathiolane Synthesis: Spirocyclic 1,3-Oxathiolanes from the Lewis-Acid-Catalyzed Reaction of Cyclic Trithiocarbonates and Oxiranes |
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| Item Type: | Journal Article, refereed, original work |
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| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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| Dewey Decimal Classification: | 540 Chemistry |
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| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
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| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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| Language: | German |
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| Date: | 1991 |
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| Deposited On: | 13 Mar 2014 08:07 |
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| Last Modified: | 10 Mar 2025 02:40 |
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| Publisher: | Wiley-Blackwell |
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| ISSN: | 0018-019X |
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| Funders: | Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche AG, Basel |
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| OA Status: | Closed |
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| Publisher DOI: | https://doi.org/10.1002/hlca.19910740714 |
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| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
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Oremus, Vladimir