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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
53
Issue
10
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.
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