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The Addition of ArSSAr to Alkenes: The Implications of a Cationic Chain Mechanism Initiated by Electrogenerated ArS(ArSSAr) +
Author(s) -
Matsumoto Kouichi,
Sanada Tomonari,
Shimazaki Hayato,
Shimada Kazuaki,
Hagiwara Shino,
Fujie Shunsuke,
Ashikari Yosuke,
Suga Seiji,
Kashimura Shigenori,
Yoshida Junichi
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300017
Subject(s) - chemistry , sulfonium , alkene , electrolysis , catalysis , cationic polymerization , chain reaction , chain (unit) , medicinal chemistry , organic chemistry , photochemistry , combinatorial chemistry , salt (chemistry) , electrode , physics , astronomy , electrolyte
Abstract The addition reactions of diaryl disulfides (ArSSAr) to alkenes and alkynes were achieved with a catalytic amount of an arylbis(arylthio)sulfonium ion (ArS(ArSSAr) + ), which was generated and accumulated by low‐temperature electrolysis of ArSSAr, to give the corresponding diarylthiolated products. The electrolysis of a mixture of ArSSAr and an alkene with a catalytic amount of electricity was also effective to drive the reactions. A cation chain mechanism mediated by ArS(ArSSAr) + as a chain carrier is suggested.