Oxidation of nitrobenzylic carbanions with dimethyldioxirane. New synthesis of quinomethanes and nitrobenzylic carbinols. First examples of methylation of carbanions with dimethyldioxirane

Authors
Makosza, M Adam, W Zhao, CG Surowiec, M
Citation
M. Makosza et al., Oxidation of nitrobenzylic carbanions with dimethyldioxirane. New synthesis of quinomethanes and nitrobenzylic carbinols. First examples of methylation of carbanions with dimethyldioxirane, J ORG CHEM, 66(15), 2001, pp. 5022-5026
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
15
Year of publication
2001
Pages
5022 - 5026
Database
ISI
SICI code
0022-3263(20010727)66:15<5022:OONCWD>2.0.ZU;2-I
Abstract
The reaction of nitrobenzylic carbanions with dimethyldioxirane (DMD) resul ts in oxidation at the carbanion center or at the nitronate center to give nitrobenzylic carbinols or quinomethanes, respectively. Minor amounts of th e methylation products are also formed. Both of these processes were observ ed for carbanions of (p-nitroaryl)diarylmethanes. The outcome of the oxidat ion process is very sensitive to the reaction conditions.