Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation

Masayuki Okajima; Kazuya Soga; Takashi Watanabe; Kimitada Terao; Toshiki Nokami; Seiji Suga; Jun Ichi Yoshida

doi:10.1246/bcsj.82.594

Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation

Masayuki Okajima, Kazuya Soga, Takashi Watanabe, Kimitada Terao, Toshiki Nokami, Seiji Suga, Jun Ichi Yoshida

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

28 Citations (Scopus)

Abstract

The "cation pools" of diarylcarbenium ions have been generated by the low-temperature electrochemical oxidation of diphenylmethane derivatives. In addition to diphenylmethanes having various substituents, 9,10-dihydroanthracene, dibenzosuberane, and xanthenes, which are annulated derivatives of diphenylmethane were also found to serve as a precursor of cation pools. The generation of the diarylcarbenium ion was confirmed by low-temperature NMR analysis and cold-spray mass analysis. Reactivity was also investigated by reactions with various carbon nucleophiles such as allyltrimethylsilane, 1,3,5-trimethylbenzene, and anisole.

Original language	English
Pages (from-to)	594-599
Number of pages	6
Journal	Bulletin of the Chemical Society of Japan
Volume	82
Issue number	5
DOIs	https://doi.org/10.1246/bcsj.82.594
Publication status	Published - Jul 1 2009
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1246/bcsj.82.594

Fingerprint Dive into the research topics of 'Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation'. Together they form a unique fingerprint.

Cite this

@article{f9cce4304ad6473ca35e8ed11aa2f835,

title = "Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation",

abstract = "The {"}cation pools{"} of diarylcarbenium ions have been generated by the low-temperature electrochemical oxidation of diphenylmethane derivatives. In addition to diphenylmethanes having various substituents, 9,10-dihydroanthracene, dibenzosuberane, and xanthenes, which are annulated derivatives of diphenylmethane were also found to serve as a precursor of cation pools. The generation of the diarylcarbenium ion was confirmed by low-temperature NMR analysis and cold-spray mass analysis. Reactivity was also investigated by reactions with various carbon nucleophiles such as allyltrimethylsilane, 1,3,5-trimethylbenzene, and anisole.",

author = "Masayuki Okajima and Kazuya Soga and Takashi Watanabe and Kimitada Terao and Toshiki Nokami and Seiji Suga and Yoshida, {Jun Ichi}",

year = "2009",

month = jul,

day = "1",

doi = "10.1246/bcsj.82.594",

language = "English",

volume = "82",

pages = "594--599",

journal = "Bulletin of the Chemical Society of Japan",

issn = "0009-2673",

publisher = "Chemical Society of Japan",

number = "5",

}

TY - JOUR

T1 - Generation of diarylcarbenium ion poolsviaelectrochemical C-H bond dissociation

AU - Okajima, Masayuki

AU - Soga, Kazuya

AU - Watanabe, Takashi

AU - Terao, Kimitada

AU - Nokami, Toshiki

AU - Suga, Seiji

AU - Yoshida, Jun Ichi

PY - 2009/7/1

Y1 - 2009/7/1

N2 - The "cation pools" of diarylcarbenium ions have been generated by the low-temperature electrochemical oxidation of diphenylmethane derivatives. In addition to diphenylmethanes having various substituents, 9,10-dihydroanthracene, dibenzosuberane, and xanthenes, which are annulated derivatives of diphenylmethane were also found to serve as a precursor of cation pools. The generation of the diarylcarbenium ion was confirmed by low-temperature NMR analysis and cold-spray mass analysis. Reactivity was also investigated by reactions with various carbon nucleophiles such as allyltrimethylsilane, 1,3,5-trimethylbenzene, and anisole.

AB - The "cation pools" of diarylcarbenium ions have been generated by the low-temperature electrochemical oxidation of diphenylmethane derivatives. In addition to diphenylmethanes having various substituents, 9,10-dihydroanthracene, dibenzosuberane, and xanthenes, which are annulated derivatives of diphenylmethane were also found to serve as a precursor of cation pools. The generation of the diarylcarbenium ion was confirmed by low-temperature NMR analysis and cold-spray mass analysis. Reactivity was also investigated by reactions with various carbon nucleophiles such as allyltrimethylsilane, 1,3,5-trimethylbenzene, and anisole.

UR - http://www.scopus.com/inward/record.url?scp=67649311813&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67649311813&partnerID=8YFLogxK

U2 - 10.1246/bcsj.82.594

DO - 10.1246/bcsj.82.594

M3 - Article

AN - SCOPUS:67649311813

VL - 82

SP - 594

EP - 599

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 5

ER -