SYNTHESIS OF α,β-UNSATURATED ALDEHYDES BY MEANS OF 3-METHOXY-1-PHENYLTHIO-1-PROPENE
SYNTHESIS OF α,β-UNSATURATED ALDEHYDES BY MEANS OF 3-METHOXY-1-PHENYLTHIO-1-PROPENE
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3-甲氧基-1-苯硫基-1-丙烯合成α,β-不饱和醛
DOI：
10.1246/cl.1977.345
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发表时间：
1977
影响因子：
1.6
通讯作者：
H. Takei
中科院分区：
文献类型：
--
作者：
M. Wada;Hideo Nakamura;T. Taguchi;H. Takei
1-苯硫基-2，3-环氧丙烷(1)在四氢呋喃中与氢化钠反应得到3-甲氧基-1-苯硫基-1-丙烯(3)，在−78℃下与二异丙胺锂反应得到3-甲氧基-1-苯硫基-1-丙烯(3)，该锂硫衍生物与卤代烷在硫原子的α位发生区域选择性反应，产物在氯化汞存在下于室温下水解生成相应的α，β不饱和醛，产率较高。
3-Methoxy-1-phenylthio-1-propene (3), obtained by the reaction of 1-phenylthio-2,3-epoxypropane (1) with sodium hydride in tetrahydrofuran (THF) and successive treatment with methyl iodide, was lithiated with lithium diisopropylamide at −78°C. The lithio derivative reacted with alkyl halides regioselectively at the α-position of sulfur atom, and hydrolysis of the products at room temperature in the presence of mercuric chloride afforded the corresponding α,β-unsaturated aldehydes in good yields.