Kinetic and mechanistic studies of NEt3-catalyzed intramolecular aminolysis of carbamate |
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Authors: | Sung Kuangsen Zhuang Bo-Ren Huang Pin-Mei Jhong Sheng-Wei |
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Affiliation: | Department of Chemistry, National Cheng Kung University, Tainan, Taiwan. kssung@mail.ncku.edu.tw |
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Abstract: | The mechanism of the NEt 3-catalyzed intramolecular aminolysis of Z- 1 in acetonitrile or aqueous acetonitrile solutions is suggested to involve rate-determining collapse of T (+/-) through simultaneous H-abstraction and ethoxide expulsion of E2 process. The evidence for that includes the primary isotope effect of k H/ k D = 1.66 in acetonitrile, general-base catalysis in aqueous buffer solutions, salt effect, and the proposed water-stabilized rate-determining transition states (TS1 and TS2) in the water-titration experiments. |
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