Rate constants for 1,n-hydrogen transfer reactions in some amino acid derived radicals |
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Authors: | Le Zeng Carl H Schiesser |
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Institution: | a School of Chemistry, The University of Melbourne, Vic. 3010, Australia b Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Vic. 3010, Australia |
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Abstract: | Absolute rate constants for 1,n-hydrogen atom transfers in some substituted amino acid derived radicals have been determined in benzene through the use of competitive kinetic experiments. Radicals derived from methyl N-(2-iodobenzoyl)-N-(tert-butyloxycarbonyl)glycinate, -alaninate, -leucinate, -tert-leucinate and -phenylglycinate undergo intramolecular 1,5-hydrogen atom transfer to afford the corresponding α-amino acid ester radicals with rate constants in the range: 1.0-4.3 × 107 s−1 at 80 °C. Where abstractable hydrogen atoms exist in the amino acid side-chain, 1,6- and 1,7-translocations are competitive processes. |
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