Journal
APPLIED RADIATION AND ISOTOPES
Volume 58, Issue 6, Pages 679-683Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0969-8043(03)00093-9
Keywords
electrochemical fluorination; nucleophilic aromatic substitution; [F-18]fluoride; radiolabeling; substituent effects
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Electrochemical fluorination of various monosubstituted aromatic compounds was performed, with [F-18]fluoride using potentiostatic anodic oxidation on platinum electrodes in an undivided cell in, acetonitrile with a mixture of Et3N . 3HF/Et3N . HCl as electrolyte. Maximum radiochemical yields were obtained after a charge. of 50 C passed the solution. The results showed a clear dependence of the radiochemical yields on the oxidation potentials E-1/2 of the substrates as a consequence of different substituents namely CH3CO-, F-, Cl-, Br- and tert.-Butyl. With increasing E-1/2, the fluorination yields decreased from 7.9% (tert.-butylbenzene) to 1.5% (acetophenone). The ratio between F.-for-X substitution and F-for-H substitution correlated with the bond energies of the C-X bond. With higher bond energies, less X-substitution was observed. (C) 2003 Elsevier Science Ltd. All rights reserved.
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