Mechanism studies on the CSI reaction with allyl ethers by varying p-substituent.
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(N)i and S(N)1 mechanism according to the stability of the carbocation. And, the only terminal allylic amine was obtained through the migration reaction in thermodynamic reaction condition.
Jung
Young Hoon
YH
Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University, Suwon 440-746, Kyonggi-Do, Korea. yhjung@skku.edu
Kim
Ji Duck
JD
D000498:Allyl Compounds / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods*; D017953:Isocyanates / Q000138:chemical synthesis*; D007723:Korea; D008738:Methyl Ethers / Q000138:chemical synthesis; D020005:Propanols / Q000138:chemical synthesis; D021281:Quantitative Structure-Activity Relationship
D000498:Allyl Compounds; D017953:Isocyanates; D008738:Methyl Ethers; D020005:Propanols; C487390:chlorosulfonyl isocyanate; C020722:cinnamyl alcohol