An experimental and theoretical investigation of the regioselective cleavage of aromatic sulfones

Authors
Botrel, A Furet, E Fourets, O Pilard, JF
Citation
A. Botrel et al., An experimental and theoretical investigation of the regioselective cleavage of aromatic sulfones, NEW J CHEM, 24(10), 2000, pp. 815-820
Citations number
28
Categorie Soggetti
Chemistry
Journal title
NEW JOURNAL OF CHEMISTRY
ISSN journal
11440546 → ACNP
Volume
24
Issue
10
Year of publication
2000
Pages
815 - 820
Database
ISI
SICI code
1144-0546(2000)24:10<815:AEATIO>2.0.ZU;2-Q
Abstract
Aromatic sulfones activated by strongly electron-withdrawing groups were re duced electrochemically. The radical anions produced were shown to be fairl y stable. Cleavage reactions are so slow that other chemical reactions (pro tonation, dimerization, etc.) may take place. A theoretical study at the B3 LYP level underlines that bond cleavage does not depend on the presence or not of electron-withdrawing groups substituted on the phenyl ring in the pa ra position.