Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Regioselective Lithiation of $\alpha$-Methylpyridine Analogue and Its Trapping Reactions with $Me_2RSiCl(R = Me, tBuCH_2(Me_3Si)CH)$

$\alpha$-Methylpyridine유도체의 국지 선택적 리튬화 반응과 $Me_2RSiCl(R = Me, tBuCH_2(Me_3Si)CH)$을 이용한 반응생성물의 확인반응

  • 김정균 (동아대학교 자연과학대학 화학과) ;
  • 박은미 (동아대학교 자연과학대학 화학과) ;
  • 손병영 (단국대학교 문리과대학 화학과)
  • Published : 19940800
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Abstract

The metallation of $\alpha$-methylpyridine 1(a∼f) with n-BuLi produced $\alpha-methylenylpyridinium$ salt 3(a∼f) by elimination of butane. The trapping reactions of 3(a∼f) with $Me_3SiCl\;and\;Me_2SiClCH(SiMe_3)CH_2tBu$ produced only 4(a∼f) and 5(a∼f). The $\alpha$-hydrogen atom of silylated methylene group in 4(a∼f) is more reactive than unreacted $CH_3$ of 4(a∼f) itself and 1(a∼f) toward n-BuLi at low temperature in pentane medium.

$\alpha$-Methylpyridine유도체1(a∼f)는 n-BuLi과의 반응에서 $\alpha$-methylenylpyridinium 염 3(a∼f)을 형성한다. 3(a∼f)와 $Me_3SiCl$ 및 $Me_2SiClCH(SiMe_3)CH_2tBu$반응에서 생성물 4(a∼f) 와 5(a∼f)을 형성한다. 화합물 4(a∼f)에 있는 규소원자와 결합된 methylene기의 수소원자는 화합물 4(a∼f)의 $CH_3$기 보다 n-BuLi과의 반응성이 큰 것으로 확인되었다.

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