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Mechanism Studies on the CSI Reaction with Allyl Ethers by Varying p-Substituent  

Jung, Young-Hoon (Organic ＆ Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University)
Kim, Ji-Duck (Organic ＆ Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University)
Publication Information
Archives of Pharmacal Research / v.26, no.9, 2003 , pp. 667-678 More about this Journal
Abstract
We examined the effect of p-substituents in p-substituted cinnamyl methyl ethers and 1-(p-substituted phenyl)allyl methyl ethers with CSI, and confirmed that the CSI reaction of allyl ethers (p-substituted ethers) is a competitive reaction of $S_Ni{\;}and{\;}S_N1$ mechanism according to the stability of the carbocation. And, the only terminal allylic amine was obtained through the migration reaction in thermodynamic reaction condition.
Keywords
Chlorosulfonyl isocyanate; Allyl ether; Carbamate;
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Times Cited By Web Of Science : 10  (Related Records In Web of Science)
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