THE CHROMIC ACID OXIDATION OF ARYL TRIFLUOROMETHYL ALCOHOLS: ISOTOPE AND SUBSTITUENT EFFECTS
- 1 February 1964
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 42 (2) , 439-446
- https://doi.org/10.1139/v64-061
Abstract
The mechanism of the chromic acid oxidation of eight aryltrmuoromethylcarbinols has been studied in acetic acid solution. Electron-donating substituents accelerate the reaction and a good correlation of rate with σ+ values has been found. The rho value is −1.01. Deuterium isotope effects for the oxidation of five of these compounds have been determined and the magnitude of the isotope effect has been found to correlate inversely with the ease of oxidation of the alcohol.The results are interpreted in terms of a unimolecular decomposition of the chromate ester of the alcohol.Keywords
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