FIRST, SERENDIPITOUS AND INTRIGUING HYDROLYSIS OF A TERTIARY NITROALKANE

Authors
CROZET MP LAPOUGE S KAAFARANI M VANELLE P
Citation
Mp. Crozet et al., FIRST, SERENDIPITOUS AND INTRIGUING HYDROLYSIS OF A TERTIARY NITROALKANE, Tetrahedron letters, 35(19), 1994, pp. 3055-3058
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
19
Year of publication
1994
Pages
3055 - 3058
Database
ISI
SICI code
0040-4039(1994)35:19<3055:FSAIHO>2.0.ZU;2-R
Abstract
The hydrolysis of imethyl-4-(1,1,2-trimethyl-2-nitropropyl)imidazole w hich leads to two tertiary alcohols formed respectively by C-NO2 and C -C bond fission, is the first example of hydrolysis of a tertiary nitr oalkane. It might be explained by an intramolecular nucleophilic catal ysis favored by a double gem-dimethyl effect and a possible anchimeric assistance by imidazole group.