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 language | English |
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Pages (from-to) | 4027-4033 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 73 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2008 Jun 6 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry