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KMID : 1059519940380080570
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Journal of the Korean Chemical Society
1994 Volume.38 No. 8 p.570 ~ p.575
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Regioselective Lithiation of α-Methylpyridine Analogue and Its Trapping Reactions with Me2RSiCl (R = Me, tBuCH2(Me3Si)CH)
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Kim Chung-Kyun
Park Eun-Mi
Son Byung-Yung
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Abstract
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The metallation of α-methylpyridine 1(a∼f) with n-BuLi produced α-methylenylpyridinium salt 3(a∼f) by elimination of butane. The trapping reactions of 3(a∼f) with Me3SiCl and Me2SiClCH(SiMe3)CH2tBu produced only 4(a∼f) and 5(a∼f). The α-hydrogen atom of silylated methylene group in 4(a∼f) is more reactive than unreacted CH3 of 4(a∼f) itself and 1(a∼f) toward n-BuLi at low temperature in pentane medium.
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