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Hochsubstituierte Cyclopentadiene mit Arylthio‐ und Arylsulfonyl‐Gruppen
Author(s) -
Hartke Klaus,
Lee KyungHee,
Massa Werner,
Schwarz Birgit
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910142
Subject(s) - cyclopentadiene , chemistry , protonation , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , ion
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.