Ilayaraja, N. and Manivel, A. and Velayutham, D. and Noel, M. (2008) The effect of substituents and operating conditions on the electrochemical fluorination of alkyl phenylacetates in Et3N4HF medium. Journal of Fluorine Chemistry, 129 (3). pp. 185-192.

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Selective electrochemical fluorination of alkyl phenylacetates (Ph–CH2–COOR, where R is methyl, ethyl, n-propyl, n-butyl, i-propyl and secbutyl) under galvanostatic conditions were reported in Et3N4HF medium. Preparative electrolysis experiments were carried out both in preelectrolysed dry Et3N4HF and the same electrolyte medium without pre-electrolysis. Very little hydrolysed fluorinated products were obtained in pre-electrolysed medium where as significant quantities of hydrolysed products leading to fluorinated phenylacetic acid were obtained from Et3N4HF without pre-electrolysis. Under optimum experimental conditions up to 87% selectivity of monofluoro ester could be achieved. Difluoro alkyl phenylacetate, monofluoro and difluoro phenylacetic acids were the other predominant side products obtained. The hydrolysis appears to be initiated by tautomeric transformation of proton after the initial electro oxidative formation of the cation radical. 19F as well as 1H NMR spectroscopy have been employed to identify the minor constituents formed during the electro oxidative process.

Item Type: Article
Uncontrolled Keywords: Selective electrochemical fluorination; Et3N4HF; Alkyl phenylacetates; a-Fluoro phenylacetates
Subjects: Electroorganic
Depositing User: ttbdu cecri
Date Deposited: 01 Apr 2012 10:53
Last Modified: 01 Apr 2012 10:53

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