Rate constants for 1,n-hydrogen transfer reactions in some amino acid derived radicals

被引：7
|
作者：
Zeng, Le
Kaouli, Talbi
Schiesser, Carl H. [1 ]
机构：
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Bio21 Mol Sci & Biotechnol Inst, Melbourne, Vic 3010, Australia
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 45期
基金：
澳大利亚研究理事会;
关键词：
D O I：
10.1016/j.tetlet.2006.09.010
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Absolute rate constants for l,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-(tertbutyloxycarbonyl)glycinate, -alaninate, -leucinate, -tert-leucinate and -phenylglycinate undergo intramolecular 1,5-hydrogen atom transfer to afford the corresponding alpha-amino acid ester radicals with rate constants in the range: 1.0-4.3 x 10(7) s(-1) at 80 degrees C. Where abstractable hydrogen atoms exist in the amino acid side-chain, 1,6- and 1,7-translocations are competitive processes. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7911 / 7914
页数：4
相关论文
共 50 条
  • [21] RATE CONSTANTS FOR REACTIONS OF HYDROGEN-ATOMS WITH SOME SILANES AND GERMANES
    AUSTIN, ER
    LAMPE, FW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 159 - 159
  • [22] SANDMEYER REACTIONS .2. ESTIMATION OF ABSOLUTE RATE CONSTANTS FOR SOME HYDROGEN-TRANSFER REACTIONS AND FOR THE TRANSFER OF WATER LIGANDS ON CU-II TO ARYL RADICALS BY USE OF A PSCHORR RADICAL CLOCK
    HANSON, P
    HAMMOND, RC
    GOODACRE, PR
    PURCELL, J
    TIMMS, AW
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (04): : 691 - 696
  • [23] REACTIONS OF HYDROGEN-ATOMS WITH HYDROPEROXYL RADICALS .1. DETERMINATION OF SPECIFIC RATE CONSTANTS OF REACTION CHANNELS
    HACK, W
    WAGNER, HG
    HOYERMANN, K
    BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1978, 82 (07): : 713 - 719
  • [24] TEMPERATURE-DEPENDENCE OF THE RATE CONSTANTS FOR ELECTRON-TRANSFER REACTIONS OF INORGANIC RADICALS
    HUIE, RE
    ALFASSI, ZB
    SHOUTE, LCT
    NETA, P
    CLIFTON, CL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 118 - PHYS
  • [25] Absolute rate constants for some intermolecular reactions of α-aminoalkylperoxyl radicals.: Comparison with alkylperoxyls
    Lalevee, Jacques
    Allonas, Xavier
    Fouassier, Jean-Pierre
    Ingold, K. U.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6489 - 6496
  • [26] RATE CONSTANTS FOR SOME REACTIONS OF FREE-RADICALS WITH HALOACETATES IN AQUEOUS-SOLUTION
    MARUTHAMUTHU, P
    PADMAJA, S
    HUIE, RE
    INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1995, 27 (06) : 605 - 612
  • [27] Enantioselective hydrogen atom transfer reactions:: Synthesis of N-acyl-α-amino acid esters
    Sibi, MP
    Asano, Y
    Sausker, JB
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (07) : 1293 - +
  • [28] Rate constants for the reactions of OH radicals with 1- and 2-bromopropane
    Teton, S.
    El Boudali, A.
    Mellouki, A.
    Journal de Chimie Physique et de Physico-Chimie Biologique, 93 (02):
  • [29] Rate constants for the reactions of OH radicals with a series of 1,4-hydroxyketones
    Baker, J
    Arey, J
    Atkinson, R
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 176 (1-3) : 143 - 148
  • [30] Rate constants for the reactions of OH radicals with 1- and 2-bromopropane
    Teton, S
    ElBoudali, A
    Mellouki, A
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1996, 93 (02) : 274 - 282
12345