O-Methylarenehydroxamates as ortho-lithiation directing groups. Titanium (III)-mediated conversion of O-methyl hydroxamates to primary amides

…, SR Stabler, S Lundberg, JM Muchowski

Index: Fisher, Lawrence E.; Caroon, Joan M.; Jahangir; Stabler, S. Russell; Lundberg, Scott; Muchowski, Joseph M. Journal of Organic Chemistry, 1993 , vol. 58, # 14 p. 3643 - 3647

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Citation Number: 36

Abstract

Reaction of 0-methyl benzohydroxamates 2a-c with sec-butyllithium in the presence of TMEDA at-40" C regiospecifically generates the highly reactive N, ortho-dilithiated species (eg 3). These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, giving adducts which on reduction with Tic13 are converted into ortho-substituted primary benzamides in excellent yields. Ortho lithiation of 0-methyl ...