Electrophilic Reaction of Phenyl Bis(Phenylthio) Sulfonium Cation as an Active Species for the Oxidative Polymerization of Diphenyl Disulfide

doi:10.1080/10601329408545869

Paper

Electrophilic Reaction of Phenyl Bis(Phenylthio) Sulfonium Cation as an Active Species for the Oxidative Polymerization of Diphenyl Disulfide

Published 1994 · E. Tsuchida, Kimihisa Yamamoto, E. Shouji

Journal of Macromolecular Science, Part A

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Abstract

Computer modeling predicts that the methyl bis(methylthio) sulfonium cation can act as an efficient electrophile for sulfide bond formation in which the sulfur atoms at the side position of the cation react with the phenyl ring of an aromatic molecule. The electrophilic reaction mechanism of phenyl bis-(phenylthio) sulfonium cation with anisole was examined using computer simulation. The reaction between phenyl bis- (phenylthio) sulfonium cation, which is a homogeneous structure of thecation, and anisole shows the efficient formation of 4-phenylthioanisole with diphenyl disulfide as a by-product. In the oxidative polymerization of diphenyl disulfide, the formation process of polyp-phenylene sulfide) includes an elementary reaction between the phenylthio group at each side position of the phenyl bis(phenylthio) sulfonium cation and the carbon at the para position of the phenyl ring.

Study Snapshot

Phenyl bis(phenylthio) sulfonium cation efficiently forms 4-phenylthioanisole with diphenyl disulfide as a by-product in the oxidative polymerization of diphenyl disulfide, resulting in polyp-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Electrophilic Reaction of Phenyl Bis(Phenylthio) Sulfonium Cation as an Active Species for the Oxidative Polymerization of Diphenyl Disulfide

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References

Acid effect on oxidative polymerization of diphenyl disulfide with DDQ

Oxidative polymerization of diphenyl disulfide with DDQ in the presence of trifluoromethane sulfonic acid involves four elementary reactions: charge transfer complex formation, oxidative reaction, sulfonium cation formation, and electrophilic substitution.

Optimization of parameters for semiempirical methods II. Applications

The new MNDO-PM3 method optimizes MNDO/AM1-type parameters for twelve elements, reducing average errors in predicted heats of formation and experimental values.

Zur Reaktion α‐halogenierter Sulfide mit Antimonpentachlorid

Antimony pentachloride reacts with (Trichlormethyl)methylsulfide to produce the carbenium salt 47, while antimony pentachloride reacts with (Chlormethyl)methylsulfide to produce chlorosulfonium salts 8 and 11.

An Efficient Synthesis of Unsymmetrical Sulfides from Organic Disulfides and Aromatic Compounds

The catalyst-mediated sulfenylation reaction of aromatic compounds with organic disulfides in 1,2-dichloroethane efficiently synthesizes unsymmetrical sulfides in high yields.

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