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: Stäb, Tobias (VerfasserIn) , Gleiter, Rolf (VerfasserIn) , Rominger, Frank (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 24 July 2002
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
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Verfasserangaben:Tobias H. Staeb, Rolf Gleiter, and Frank Rominger

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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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