COMPARATIVE REACTIVITIES OF TRIFLUOROMETHYL-SUBSTITUTED AND PENTAFLUOROETHYL-SUBSTITUTED VINYL ETHERS IN ACID-CATALYZED HYDRATION

Authors
BEGUE JP BENAYOUD F BONNETDELPON D ALLEN AD COX RA TIDWELL TT
Citation
Jp. Begue et al., COMPARATIVE REACTIVITIES OF TRIFLUOROMETHYL-SUBSTITUTED AND PENTAFLUOROETHYL-SUBSTITUTED VINYL ETHERS IN ACID-CATALYZED HYDRATION, Gazzetta chimica italiana, 125(9), 1995, pp. 399-402
Citations number
46
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
125
Issue
9
Year of publication
1995
Pages
399 - 402
Database
ISI
SICI code
0016-5603(1995)125:9<399:CROTAP>2.0.ZU;2-3
Abstract
The protonation of fluorinated alkenes shows a greater retardation by a factor of 2.8 by C2F5 compared to CF3 substituents in carbocation fo rmation, and larger k(H)/k(alpha-Rf) rate ratios compared to solvolysi s reactions, a result ascribable to ground-state steric and electronic destabilization of the solvolysis substrates.