Preparation and structures of cyclic tetrathiadienes and tetrathiaenynes
Through the use of diisobutylaluminium hydride (DIBAH) we were able to reduce selectively the triple bond(s) of the following cyclic diynes: 1,4,7,10-tetrathiacyclodeca-2,8-diyne (1), 1,4,8,11-tetrathiacyclotetradeca-2,9-diyne (2), 1,4,9,12-tetrathiacyclohexadeca-2,10-diyne (3), 1,4,10,13-tetrathiac...
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| Hauptverfasser: | , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
24 July 2002
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| In: |
European journal of organic chemistry
Year: 2002, Heft: 16, Pages: 2815-2822 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200208)2002:16<2815::AID-EJOC2815>3.0.CO;2-9 |
| Online-Zugang: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200208)2002:16<2815::AID-EJOC2815>3.0.CO;2-9 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200208%292002%3A16%3C2815%3A%3AAID-EJOC2815%3E3.0.CO%3B2-9 |
| Verfasserangaben: | Tobias H. Staeb, Rolf Gleiter, and Frank Rominger |
MARC
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| 520 | |a Through the use of diisobutylaluminium hydride (DIBAH) we were able to reduce selectively the triple bond(s) of the following cyclic diynes: 1,4,7,10-tetrathiacyclodeca-2,8-diyne (1), 1,4,8,11-tetrathiacyclotetradeca-2,9-diyne (2), 1,4,9,12-tetrathiacyclohexadeca-2,10-diyne (3), 1,4,10,13-tetrathiacyclooctadeca-2,11-diyne (4), 1,4,11,14-tetrathiacycloeicosa-2,12-diyne (5), 1,4,8,11-tetrathiacycloheptadeca-2,9-diyne (6), and 7,16-dioxa-1,4,10,13-tetrathiacyclooctadeca-2,11-diyne (7). The resulting cyclic enynes 8−14 and cyclic dienes 15−20 were isolated and characterized by their analytical data. In the cases of 8, 10, 11, 14, and 15−20 we were able to isolate single crystals, which were investigated by X-ray diffraction. For all molecular structures we found stair-like conformations. These shapes of the molecules were traced back to the zigzag arrangements of the hydrocarbon chains and the rigid building units (S−CH=CH−S) and/or (S−C≡C−S). In the solid-state forms of 11, 16, 17, and 19 we encountered columnar structures caused by close contacts between sulfur centers of neighboring rings. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) | ||
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