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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 38, Number 8
JKCSEZ 38(8)
April 20, 1994 

Regioselective Lithiation of α-Methylpyridine Analogue and Its Trapping Reactions with Me2RSiCl (R = Me, tBuCH2(Me3Si)CH)

α-Methylpyridine유도체의 국지 선택적 리튬화 반응과 Me2RSiCl(R = Me, tBuCH2(Me3Si)CH)을 이용한 반응생성물의 확인반응
Chung-Kyun Kim, Eunmi Park, Byung-Yung Son

김정균, 박은미, 손병영
α-Methylpyridine유도체1(a∼f)는 n-BuLi과의 반응에서 α-methylenylpyridinium 염 3(a∼f)을 형성한다. 3(a∼f)와 Me3SiCl 및 Me2SiClCH(SiMe3)CH2tBu반응에서 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 CH3기 보다 n-BuLi과의 반응성이 큰 것으로 확인되었다.

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.

570 - 575
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