Abstract
The reaction of 4,4-dimethyl-1,3-thiazole-5(4H)-thiones 7a-c with dimethyl 2-diazo-3-(phenylamino)butanoate (2), prepared from dimethyl fumarate and phenyl azide, in toluene at 80°C yielded mixtures of dimethyl 2-(4,5-dihydro-4,4-dimethyl-1,3-thiazol-5-ylidene)-3-(N-phenylamino)butanedioates of type 11 and four diastereoisomeric 4,4-dimethyl-9-phenyl-1,6-dithia-3,9-diazaspiro[4.4]non-2-ene-7,8-dicarboxylates of type 12. The formation of the products of type 12 is rationalized by a novel cyclization of intermediate thiocabonyl ylides 9. The structures of cis-12a, cis-12c, and trans-12c were established by X-ray crystallography.
| 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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| Language: | English |
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| Date: | 1999 |
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| Deposited On: | 05 Nov 2013 16:50 |
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| Last Modified: | 10 Jan 2025 02:38 |
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| Publisher: | Polskie Towarzystwo Chemiczne |
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| ISSN: | 0137-5083 |
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| Funders: | Polish State Committee for Scientific Research, Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Dr. Helmut Legerlotz-Stiftung, Universität Zürich |
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| OA Status: | Closed |
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| Project Information: | - Funder:
- Grant ID:
- Project Title: Polish State Committee for Scientific Research
- Funder: SNSF
- Grant ID:
- Project Title: Swiss National Science Foundation
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
- Funder:
- Grant ID:
- Project Title: Dr. Helmut Legerlotz-Stiftung, Universität Zürich
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Romanski, Jaroslaw