Hochsubstituierte Cyclopentadiene mit Arylthio- und Arylsulfonyl-Gruppen

✍ Scribed by Hartke, Klaus ;Lee, Kyung-Hee ;Massa, Werner ;Schwarz, Birgit

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 944 KB
• Volume: 1991
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199119910142

✦ Synopsis

Highly Substituted Cyclopentadienes with Arylthio and Arylsulfonyl Groups

Cyclopentadienes 1 react with diaryl disulfides 2 to form the tetrakis(arylthio)cyclopentadienides 3, which have been oxidized with m‐chloroperbenzoic acid to give the tetrakis(arylsulfonyl)cyclopentadienides 5. Protonation of 5 yields the tetrakis(arylsulfonyl)cyclopentadienes 7 by migration of arylsulfonyl groups. Oxidation of 3 by iodine leads to the dihydropentafulvalenes 11. By reaction of 3 with arylthiosulfonates 14 the pentakis(arylthio)cyclopentadienes 15 have been obtained. Their salts 16 may be oxidized to form the pentakis(arylsulfonyl)cyclopentadienides 17, or condensed with sulfenyl chlorides to give the hexakis(arylthio)cyclopentadienes 19. The structure of the phenylthio compound 19a was confirmed by an X‐ray structure analysis.