Phenoxide-directed ortho lithiation

GH Posner, KA Canella

Index: Posner, Gary H.; Canella, Karen A. Journal of the American Chemical Society, 1985 , vol. 107, # 8 p. 2571 - 2573

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Citation Number: 65

Abstract

Communications to the Editor and potassium (KH) I2 phenoxides before adding tert- butyllithium resulted in lower yields of silyl adduct 2. Using 2-methyltetrahydropyran in an attempt to diminish tert-butyllithium reaction with the solvent13 offered no advantage over using THP itself. Quenching ortho-lithiated phenolate 1 with such electrophiles as methyl iodide7b (or dimethyl sulfate), carbon dioxide, benzoic anhydride, and carbon tetrabr~ ...