Tethered dithiacyclopropenones: syntheses and structural properties of tetrathiacyclopropenonophanes
The reaction of the cyclic tetrathiadiynes 4(m.n) (where m and n indicate the number of methylene groups between the dithiaacetylene units) with sodium trichloroacetate and subsequent hydrolysis of the gem-dichlorocyclopropenes afforded the mono- and biscyclopropenone derivatives 5(m.n) and 6(m.n) i...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
04/14/2001
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| In: |
The journal of organic chemistry
Year: 2001, Volume: 66, Issue: 10, Pages: 3416-3422 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo001721j |
| Online Access: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1021/jo001721j Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/jo001721j 
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| Author Notes: | Daniel B. Werz, Frank Rominger, Isabella Hyla-Kryspin, and Rolf Gleiter |
| Summary: | The reaction of the cyclic tetrathiadiynes 4(m.n) (where m and n indicate the number of methylene groups between the dithiaacetylene units) with sodium trichloroacetate and subsequent hydrolysis of the gem-dichlorocyclopropenes afforded the mono- and biscyclopropenone derivatives 5(m.n) and 6(m.n) in moderate yields. Investigation of the X-ray crystal structures revealed small torsion angles between the CH2−S bond and the C−C double bond, indicating conjugation between the sulfur 3p lone pair and the cyclopropenone ring. The maintenance of the conjugation determines the secondary structure of both (5, 6) ring systems. |
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| Item Description: | Gesehen am 13.11.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo001721j |