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The oxidation of substituted benzyl alcohols by bis(trifluoroacetoxy)iodo] benzene in aqueous acetic acid solution results in the formation of the corresponding benzaldehydes. The reaction is first order with respect to each of the alcohol, TFAIB and hydrogen ions. The oxidation of [1,1-2H 2]benzyl alcohol exhibited the presence of a substantial primary kinetic isotope effect, indicating the cleavage of the alpha-C-H bond in the rate-determining step. Increase in the amount of water, in the solvent mixture of acetic acid and water, results in a decrease of the reaction rate. The analysis of the substituent effect in terms of Charton’s LDR equation yielded an excellent correlation with negative reaction constants. A mechanism involving a hydride-ion transfer in the rate-determining step has been proposed.
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Reference：
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles