An electroinitiated cation chain reaction: Intramolecular carbon-carbon bond formation between thioacetal and olefin groups

Kouichi Matsumoto; Shunsuke Fujie; Koji Ueoka; Seiji Suga; Jun Ichi Yoshida

doi:10.1002/anie.200705748

An electroinitiated cation chain reaction: Intramolecular carbon-carbon bond formation between thioacetal and olefin groups

Kouichi Matsumoto, Shunsuke Fujie, Koji Ueoka, Seiji Suga, Jun Ichi Yoshida

Research output: Contribution to journal › Article › peer-review

52 Citations (Scopus)

Abstract

(Figure Presented) The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)-⁺B(C₆F⁵) 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.

Original language	English
Pages (from-to)	2506-2508
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	13
DOIs	https://doi.org/10.1002/anie.200705748
Publication status	Published - Mar 14 2008
Externally published	Yes

Keywords

Carbocations
Electrochemistry
Oxidation
Sulfur
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.200705748

Cite this

@article{eafe069d1cea444784efca93d2611789,

title = "An electroinitiated cation chain reaction: Intramolecular carbon-carbon bond formation between thioacetal and olefin groups",

abstract = "(Figure Presented) The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)-+B(C6F5) 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.",

keywords = "Carbocations, Electrochemistry, Oxidation, Sulfur, Synthetic methods",

author = "Kouichi Matsumoto and Shunsuke Fujie and Koji Ueoka and Seiji Suga and Yoshida, {Jun Ichi}",

year = "2008",

month = mar,

day = "14",

doi = "10.1002/anie.200705748",

language = "English",

volume = "47",

pages = "2506--2508",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "13",

}

TY - JOUR

T1 - An electroinitiated cation chain reaction

T2 - Intramolecular carbon-carbon bond formation between thioacetal and olefin groups

AU - Matsumoto, Kouichi

AU - Fujie, Shunsuke

AU - Ueoka, Koji

AU - Suga, Seiji

AU - Yoshida, Jun Ichi

PY - 2008/3/14

Y1 - 2008/3/14

N2 - (Figure Presented) The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)-+B(C6F5) 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.

AB - (Figure Presented) The treatment of an olefinic thioacetal with a catalytic amount of ArS(ArSSAr)-+B(C6F5) 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.

KW - Carbocations

KW - Electrochemistry

KW - Oxidation

KW - Sulfur

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=53549091872&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=53549091872&partnerID=8YFLogxK

U2 - 10.1002/anie.200705748

DO - 10.1002/anie.200705748

M3 - Article

C2 - 18286560

AN - SCOPUS:53549091872

SN - 1433-7851

VL - 47

SP - 2506

EP - 2508

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 13

ER -

An electroinitiated cation chain reaction: Intramolecular carbon-carbon bond formation between thioacetal and olefin groups

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this