Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

Jesus Iniesta; Hannah Alcock; David J. Walton; Masataka Watanabe; Shuntaro Mataka; Thies Thiemann

doi:10.1016/j.electacta.2006.03.001

Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

Jesus Iniesta, Hannah Alcock, David J. Walton, Masataka Watanabe, Shuntaro Mataka, Thies Thiemann

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

13 Citations (Scopus)

Abstract

The electrooxidative behaviour of tetraphenylcyclopentadienone (tetracyclone) and a number of its substituted derivatives have been studied by cyclic voltammetry. Preparative electrooxidation reactions have been found for the tetracyclones to yield the corresponding α-pyrones as major product from an oxygen insertion reaction; while in contrast, under similar conditions the sulfoxy analogue, tetraphenylthiophene-S-oxide, is oxidized to (Z)-diphenacylstilbene with loss of the sulfur-function from the heteroaromatic ring.

Original language	English
Pages (from-to)	5682-5690
Number of pages	9
Journal	Electrochimica Acta
Volume	51
Issue number	26
DOIs	https://doi.org/10.1016/j.electacta.2006.03.001
Publication status	Published - Aug 15 2006
Externally published	Yes

Keywords

Desulfurisation
Electrooxidation
Oxygen insertion
Tetraarylcyclopentadienone
Tetracyclone
Thiophene-S-oxide

ASJC Scopus subject areas

General Chemical Engineering
Electrochemistry

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10.1016/j.electacta.2006.03.001

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title = "Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide",

abstract = "The electrooxidative behaviour of tetraphenylcyclopentadienone (tetracyclone) and a number of its substituted derivatives have been studied by cyclic voltammetry. Preparative electrooxidation reactions have been found for the tetracyclones to yield the corresponding α-pyrones as major product from an oxygen insertion reaction; while in contrast, under similar conditions the sulfoxy analogue, tetraphenylthiophene-S-oxide, is oxidized to (Z)-diphenacylstilbene with loss of the sulfur-function from the heteroaromatic ring.",

keywords = "Desulfurisation, Electrooxidation, Oxygen insertion, Tetraarylcyclopentadienone, Tetracyclone, Thiophene-S-oxide",

author = "Jesus Iniesta and Hannah Alcock and Walton, {David J.} and Masataka Watanabe and Shuntaro Mataka and Thies Thiemann",

note = "Funding Information: This research is part of an EPSRC project, UK (Grant No: GR/S41982/01). J. Iniesta wishes to thank EPSRC and the Ministry of Science and Technology (Ramon y Cajal Programme), Spain, for their financial support. We also gratefully acknowledge Dr. P. Candela and Y. Tanaka for their analytical support.",

year = "2006",

month = aug,

day = "15",

doi = "10.1016/j.electacta.2006.03.001",

language = "English",

volume = "51",

pages = "5682--5690",

journal = "Electrochimica Acta",

issn = "0013-4686",

publisher = "Elsevier Ltd",

number = "26",

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TY - JOUR

T1 - Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

AU - Iniesta, Jesus

AU - Alcock, Hannah

AU - Walton, David J.

AU - Watanabe, Masataka

AU - Mataka, Shuntaro

AU - Thiemann, Thies

N1 - Funding Information: This research is part of an EPSRC project, UK (Grant No: GR/S41982/01). J. Iniesta wishes to thank EPSRC and the Ministry of Science and Technology (Ramon y Cajal Programme), Spain, for their financial support. We also gratefully acknowledge Dr. P. Candela and Y. Tanaka for their analytical support.

PY - 2006/8/15

Y1 - 2006/8/15

N2 - The electrooxidative behaviour of tetraphenylcyclopentadienone (tetracyclone) and a number of its substituted derivatives have been studied by cyclic voltammetry. Preparative electrooxidation reactions have been found for the tetracyclones to yield the corresponding α-pyrones as major product from an oxygen insertion reaction; while in contrast, under similar conditions the sulfoxy analogue, tetraphenylthiophene-S-oxide, is oxidized to (Z)-diphenacylstilbene with loss of the sulfur-function from the heteroaromatic ring.

AB - The electrooxidative behaviour of tetraphenylcyclopentadienone (tetracyclone) and a number of its substituted derivatives have been studied by cyclic voltammetry. Preparative electrooxidation reactions have been found for the tetracyclones to yield the corresponding α-pyrones as major product from an oxygen insertion reaction; while in contrast, under similar conditions the sulfoxy analogue, tetraphenylthiophene-S-oxide, is oxidized to (Z)-diphenacylstilbene with loss of the sulfur-function from the heteroaromatic ring.

KW - Desulfurisation

KW - Electrooxidation

KW - Oxygen insertion

KW - Tetraarylcyclopentadienone

KW - Tetracyclone

KW - Thiophene-S-oxide

UR - http://www.scopus.com/inward/record.url?scp=33746591650&partnerID=8YFLogxK

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U2 - 10.1016/j.electacta.2006.03.001

DO - 10.1016/j.electacta.2006.03.001

M3 - Article

AN - SCOPUS:33746591650

SN - 0013-4686

VL - 51

SP - 5682

EP - 5690

JO - Electrochimica Acta

JF - Electrochimica Acta

IS - 26

ER -

Electrochemical oxidation of tetracyclones and tetraphenylthiophene-S-oxide

Abstract

Keywords

ASJC Scopus subject areas

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