Kinetic isotope effects for the C-H activation step in phase-transfer halogenations of alkanes

Authors
Lauenstein, O Fokin, AA Schreiner, PR
Citation
O. Lauenstein et al., Kinetic isotope effects for the C-H activation step in phase-transfer halogenations of alkanes, ORG LETT, 2(15), 2000, pp. 2201-2204
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
15
Year of publication
2000
Pages
2201 - 2204
Database
ISI
SICI code
1523-7060(20000727)2:15<2201:KIEFTC>2.0.ZU;2-6
Abstract
[GRAPHICS] Within the scope of phase-transfer halogenations (Br and I) of alkanes, sig nificant HID kinetic isotope effects (KIE = 4-5) indicate that hydrogen abs traction is rate limiting. The excellent agreement of computed and experime ntally determined H/D KIE as well as trapping experiments support the invol vement of trihalomethyl radicals in the activation step.