ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The oxidation of 1-phenyl-2,2,2-trifluoroethanol (ROH) with potassium permanganate in 0.2 M aqueous sodium hydroxide solution at 25 °C provides 2,2,2-trifluoroacetophenone as the sole product. The reaction rate constant, which was measured under pseudo-first order conditions by following the decrease in substrate concentration as a function of time, was found to be substantially smaller than previously reported. The primary kinetic deuterium isotope effect was measured as k2H/k2D = 14·7 ± 1·0. A hydrogen-transfer mechanism involving significant tunnelling is proposed. The oxidation of 1-phenylethanol under similar reaction conditions yields acetophenone as the initial product. The kinetic deuterium isotope effect was found to be k2H/k2D = 5·2 ± 0·8.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610080309