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Note | Regular issue | Vol 63, No. 12, 2004, pp.2863-2868
Published online, 29th October, 2004
DOI: 10.3987/COM-04-10229
Electrophilic Reaction of N-Lewis Acid and N-Oxide Lewis Acid Complexes of 4-Methylpyridines and Their N-Oxides through Base-induced Deprotonation

Yoshinobu Tagawa,* Manami Nomura, Kenji Yamagata, Daisuke Teshima, Kazuhiko Shibata, and Yohinobu Goto

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan


The comparative studies were carried out on the relative reactivity of 4-methylpyridines, their N-oxides and their Lewis acid complexes towards electrophilic reaction. α-Deprotonation in pyridine ring rather than deprotonation of active methyl group or metal-halogen exchange occurred preferentially in the reaction of N- and N-oxides BF3 complexes with electrophile in the presence of LTMP-TMEDA in THF to give α-substituted-4-methylpyridines and their N-oxides.