Alkyl- and aryl-thiolation : a kinetic study with bis-phenylsulfonylmethane

J.K. Bosscher, H. Kloosterziel

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4 Citations (Scopus)

Abstract

The kinetics of the reaction of bis(phenylsulfonyl)methane with thiosulfonic esters (RSSO2R') were measured in 100% ethanol, in the presence of triethylamine, at 20 Deg. The kinetic data on the substitution of an active hydrogen by a thioaryl or thioalkyl (RS) group are compatible with a two-step mechanism. First the carbanion of bis(phenylsulfonyl)methane is formed by action of the base after which a bimol. reaction occurs between the carbanion and the thiosulfonate. The reaction is retarded by introduction of electron donating substituents in both R and R'. The possible structure of the transition state is discussed. [on SciFinder (R)]
Original languageEnglish
Pages (from-to)402-412
JournalRecueil des Travaux Chimiques des Pays-Bas
Volume89
Issue number4
DOIs
Publication statusPublished - 1970

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