Kinetic and mechanistic studies of NEt3-catalyzed intramolecular aminolysis of carbamate

Kuang-Sen Sung, Bo Ren Zhuang, Pin Mei Huang, Sheng Wei Jhong

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10 Citations (Scopus)

Abstract

(Graph Presented) The mechanism of the NEt3-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 kH/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.

Original languageEnglish
Pages (from-to)4027-4033
Number of pages7
JournalJournal of Organic Chemistry
Volume73
Issue number11
DOIs
Publication statusPublished - 2008 Jun 6

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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