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Vicarious Michael Addition

Vicarious Michael Addition
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摘要 C-H bond can undergo vicarious Michael addition reaction (VMA) with doubleactivated double bond in the absence of strong base and catalyst under mild conditions. Intramolecular H-bonding, electron-withdrawing inductive effect, and steric hindrance at aposition of nucleophile facilitates C-H addition over N-H addition. By using VMA, high branching multiplicity, novel branching pattern, controllable density and distribution of functional groups can be envisioned for novel dendrimer synthesis. C-H bond can undergo vicarious Michael addition reaction (VMA) with doubleactivated double bond in the absence of strong base and catalyst under mild conditions. Intramolecular H-bonding, electron-withdrawing inductive effect, and steric hindrance at aposition of nucleophile facilitates C-H addition over N-H addition. By using VMA, high branching multiplicity, novel branching pattern, controllable density and distribution of functional groups can be envisioned for novel dendrimer synthesis.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2006年第4期561-564,共4页 中国化学快报(英文版)
关键词 Michael addition DENDRIMERS C-H bond activation hydrogen bonds synthesis. Michael addition, dendrimers, C-H bond activation, hydrogen bonds, synthesis.
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  • 1[1]A.Michael,J.Prakt.Chem.,1887,35,349.
  • 2[2]T.C.Wabnitz,J.Q.Yu,and J.B.Spencer,Chem.Eur.J.,2004,10,484.And the references cited therein.
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  • 4[4]The result was obtained when cyclohexyl amine was added into the acetonitrile solution of diethyl methylenemalonate.With the reverse addition order,i.e.adding diethyl methylenemalonate into the amine solution,the content of 1:2 adduct was slightly reduced with a ratio of 7:3 (products 1cyclohex versus 2cyclohex).

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