Stereoselective formation of allyl ethers by reaction of epoxides with organic chlorides under liquid-solid phase-transfer catalysis.
XP Gu, I Ikeda, M Okahara
Index: Gu, Xue-Ping; Ikeda, Isao; Okahara, Mitsuo Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 2 p. 667 - 672
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Citation Number: 15
Abstract
A series of trans-3-chloroallyl ethers and trans-3-thioallyl ethers were stereoselectively synthesized in one step by the reaction of 1-chloro-2, 3-epoxypropane or 2, 3-epoxypropyl sulfides with alkyl chlorides in the presence of solid sodium hydroxide and quaternary ammonium salt as a phase-transfer catalyst. Phase-transfer catalytic hydroxide ion-initiation followed by stereoselective isomerization of the epoxide ring through β-elimination is ...
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