V. Suryanarayanan et M. Noel, SELECTIVE ELECTROFLUORINATION OF PHENYLACETONITRILE AND ALPHA-(PHENYLTHIO)ACETONITRILE - THE ROLE OF SULFUR AND OTHER OPERATING PARAMETERS, Journal of fluorine chemistry, 91(2), 1998, pp. 153-157
Cyclic voltammetric and constant current electrolysis were employed to
study the electrochemical fluorination of PhCH2CN and PhSCH2CN in Et3
N . 3HF/CH3CN using Pt electrodes. The presence of a sulfur atom near
the methylene group in PhSCH2CN ensures the oxidative fluorination of
this compound at much lower potential (around 1.75 V) when compared to
PhCH2CN (2.0 V in solvent-free Et3N . 3HF). Operating parameters such
as drying the solvent, pre-electrolysis, polarity reversal, temperatu
re, current density, and concentration of HF as well as Et3N in CH3CN
medium show significant influence on the overall yield of more easily
oxidisable PhSCH2CN when compared to PhCH2CN. Maximum yields of 23% in
the case of PhCHFCN and 61% in the case of PhSCHFCN were achieved. (C
) 1998 Elsevier Science S.A. All rights reserved.