Syntheses and structural properties of cyclic tetrathiadiynes
The four-component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34, 38, 41, and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The result...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) Festschrift |
| Language: | English |
| Published: |
03 July 2000
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| In: |
European journal of organic chemistry
Year: 2000, Issue: 13, Pages: 2479-2488 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9 |
| Subjects: | |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/1099-0690%28200007%292000%3A13%3C2479%3A%3AAID-EJOC2479%3E3.0.CO%3B2-9 
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| Author Notes: | Christoph Benisch, Sabine Bethke, Rolf Gleiter, Thomas Oeser, Hans Pritzkow, and Frank Rominger |
| Summary: | The four-component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34, 38, 41, and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The resulting tetrathiacyclodiynes 25−44 were investigated by X-ray analysis. For ring systems with a twist-chair conformation the torsion angle between the CH2−S σ-bonds of the CH2−S−C≡C−S−CH2 moiety adopts values between 75° and 110°. These values are due to electronic effects, as shown by HF/6-31G* calculations. |
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| Item Description: | Dedicated to Professor Franz Effenberger on the occasion of his 70th birthday Gesehen am 27.10.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/1099-0690(200007)2000:13<2479::AID-EJOC2479>3.0.CO;2-9 |