Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4957942

Reference Type

Journal Article

Title

Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media

Author(s)

Prigent, S; Cauliez, P; Simonet, J; Peters, DG

Year

1999

Is Peer Reviewed?

Yes

Journal

Acta Chemica Scandinavica
ISSN: 0904-213X
EISSN: 1902-3103

Volume

Issue

Page Numbers

892-900

DOI

10.3891/acta.chem.scand.53-0892

Web of Science Id

WOS:000083106400020

Abstract

1-Cycloalken-1-yl phenyl sulfones la and Ib have been studied electrochemically in aprotic media (N,N-dimethylformamide, dimethyl sulfoxide, or acetonitrile containing tetraalkylammonium salts) at a mercury electrode. Their behaviour has been compared with that of 2-norbornen-2-yl phenyl sulfone Ic. The expected cleavage reaction is accompanied by a concomitant isomerization process into allyl sulfones that is triggered by electrogenerated bases. A quantitative determination of the product distribution during controlled-potential electrolyses suggests the formation of dimers and oligomeric species, arising through a Michael addition of the sulfone anions to the activated double bond of these sulfones.