Relative Basicities of ortho-, meta-, and para-Substituted Aryllithiums

J Gorecka-Kobylinska, M Schlosser

Index: Gorecka-Kobylinska, Joanna; Schlosser, Manfred Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 222 - 229

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Citation Number: 14

Abstract

The relative basicities of aryllithiums bearing methoxy, chlorine, fluorine, trifluoromethyl and trifluoromethoxy substituents at the ortho, meta, and para positions have been assessed. To this end, two aryllithiums of comparable basicity were equilibrated together with the corresponding bromo-or iodoarenes in a 1: 2 mixture of pentanes with tetrahydrofuran at− 50,− 75, or− 100° C. The “basicity”(protodelithiation) increments ΔΔ G derived from the ...