On the mechanism of the dimethyldioxirane oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions

Authors
Adam, W Makosza, M Zhao, CG Surowiec, M
Citation
W. Adam et al., On the mechanism of the dimethyldioxirane oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions, J ORG CHEM, 65(4), 2000, pp. 1099-1101
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
4
Year of publication
2000
Pages
1099 - 1101
Database
ISI
SICI code
0022-3263(20000225)65:4<1099:OTMOTD>2.0.ZU;2-0
Abstract
The mechanism of the novel dimethyldioxirane (DMD) oxidation of sigma(H) ad ducts (Meisenheimer complexes) generated from nitroarenes and carbanions wa s elucidated. The proposed mechanism, which is akin to that of the oxidativ e Nef reaction, is supported by the isolation of the cyclohexadienone inter mediate and the lack of a primary kinetic isotopic effect. Protic solvents (H2O, MeOH) enhance the reactivity of DMD through intermolecular hydrogen b onding.