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An Electroinitiated Cation Chain Reaction: Intramolecular Carbon–Carbon Bond Formation between Thioacetal and Olefin Groups
Author(s) -
Matsumoto Kouichi,
Fujie Shunsuke,
Ueoka Koji,
Suga Seiji,
Yoshida Junichi
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705748
Subject(s) - intramolecular force , thioacetal , olefin fiber , chemistry , carbon fibers , carbon chain , carbon–carbon bond , stereochemistry , organic chemistry , catalysis , acetal , materials science , composite number , composite material
The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr) + B(C 6 F 5 ) 4 − , or the electrolysis of a mixture of an olefinic thioacetal and ArSSAr, gives rise to effective intramolecular carbon–carbon bond formation (see scheme). This transformation opens up great potential for electroinitiated cation chain reactions in organic synthesis.