Tethered dithiacyclopropenones

• Verfasst von: Werz, Daniel B. [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hyla-Kryspin, Isabella [VerfasserIn]
• Verfasst von: Gleiter, Rolf [VerfasserIn]
• Titel: Tethered dithiacyclopropenones
• Titelzusatz: syntheses and structural properties of tetrathiacyclopropenonophanes
• Verf.angabe: Daniel B. Werz, Frank Rominger, Isabella Hyla-Kryspin, and Rolf Gleiter
• E-Jahr: 2001
• Jahr: 04/14/2001
• Umfang: 7 S.
• Fussnoten: Gesehen am 13.11.2020
• Titel Quelle: Enthalten in: The journal of organic chemistry
• Ort Quelle: [S.l.] : American Chemical Society, 1936
• Jahr Quelle: 2001
• Band/Heft Quelle: 66(2001), 10, Seite 3416-3422
• ISSN Quelle: 1520-6904
• DOI: doi:10.1021/jo001721j
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1738681181

Abstract

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.