Journal of fluorine chemistry

High pressure nucleophilic fluoride-ion substitution reactions: formation of fluoroalkylbenzenes

JM Gerdes, RN Keil, AT Shulgin, CA Mathis

Index: Gerdes, John M.; Keil, Robert N.; Shulgin, Alexander T.; Mathis, Chester A. Journal of Fluorine Chemistry, 1996 ,  vol. 78,  # 2  p. 121 - 129

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Citation Number: 8

Abstract

A series of 1-phenyl-2-tosyloxy-and 1-phenyl-3-tosyloxyalkanes was synthesized and then subjected to tetrabutylammonium fluoride in THF under 15 kbar (1.5 GPa), 8 kbar or 1 bar pressures. The resultant substitution and elimination reaction product distributions were analyzed. The application of pressure enhanced the progress of the fluoride-ion substitution reactions. The degree of selectivity of the one reaction over the other was found to be a ...