Isomerisation reaction of a gem-bis-trifluoromethyl olefin in a basic medium: a kinetic study

Citation
M. Tordeux et al., Isomerisation reaction of a gem-bis-trifluoromethyl olefin in a basic medium: a kinetic study, J FLUORINE, 111(2), 2001, pp. 147-152
Citations number
17
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
JOURNAL OF FLUORINE CHEMISTRY
ISSN journal
00221139 → ACNP
Volume
111
Issue
2
Year of publication
2001
Pages
147 - 152
Database
ISI
SICI code
0022-1139(20011028)111:2<147:IROAGO>2.0.ZU;2-T
Abstract
The rearrangement of 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-2-ene to 5-phenyl-1,1,1-trifluoro-2-(trifluoromethyl)pent-3-ene has been studied by F-19 NMR in dimethylsulphoxide (DMSO). This isomerisation is catalysed by a base such as triethylamine. It is apparent that the olefin is more sta ble when the two trifluoromethyl groups are placed on a saturated carbon ra ther than on a vinylic carbon. In the isomerisation process, the part of tr iethylamine is to assist the intramolecular hydrogen transfer to give the m ore stable isomer. (C) 2001 Elsevier Science B.V. All rights reserved.