Journal of fluorine chemistry

A simple method for the displacement of bromine by fluorine at tertiary, benzylic or non-classical secondary sites

F Leroux, L Garamszegi, M Schlosser

Index: Leroux, Frederic; Garamszegi, Laszlo; Schlosser, Manfred Journal of Fluorine Chemistry, 2002 , vol. 117, # 2 p. 177 - 180

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Citation Number: 5

Abstract

Iodine fluoride or, being its operational equivalent, the mixture of N-iodosuccinimide and triethylamine tris (hydrogen fluoride) reacts with tertiary and benzylic bromoalkanes to afford the respective fluoroalkanes in moderate-to-excellent yields. In contrast, primary bromoalkanes are virtually inert under identical conditions. Secondary bromoalkanes do not react either unless the heterolytically generated cationic intermediates benefit from non- ...