The Reactivity of 2??Fluoro??and 2??Chloropyridines toward Sodium Ethoxide: Factors Governing the Rates of Nucleophilic (Het) Aromatic Substitutions

M Schlosser, T Rausis

Index: Schlosser, Manfred; Rausis, Thierry Helvetica Chimica Acta, 2005 , vol. 88, # 6 p. 1240 - 1249

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Citation Number: 20

Abstract

Abstract The relative displacement rates of the halide substituent from 2-fluoro-and 2- chloropyridines by EtONa in EtOH at+ 25 were assessed by competition kinetics. The 2- fluoropyridine reacts 320 times faster than the chloro analog. A CF 3 group increases the reactivity more than single halogen atoms do, whatever the element, and the latter are superior to Me 3 Si groups. Substituents accommodated at the 4-position operate through ...