31P NMR kinetic study of the tandem cleavage of phosphonate esters by bromotrimethylsilane

被引:8
作者
Conibear, Anne C.
Lobb, Kevin A.
Kaye, Perry T. [1 ]
机构
[1] Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
基金
英国医学研究理事会; 新加坡国家研究基金会;
关键词
Phosphorus-31; NMR; Phosphonate esters; Kinetics; Bromotrimethylsilane; REDUCTOISOMERASE INHIBITORS; ANTIMALARIAL-DRUGS; BIOSYNTHESIS; CALIBRATION; PHOSPHATE; PATHWAY; PROBE;
D O I
10.1016/j.tet.2010.08.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
H-1 and P-31 NMR methods have been used to access rate constants and activation parameters for each of the consecutive second-order silylation reactions involved in the overall transformation (1a -> 3a -> 4a), while computational optimisation of the rate constants obtained from the initial, linear phase of each reaction has permitted an excellent fit with the experimental data for the entire course of the reaction. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8446 / 8449
页数:4
相关论文
共 16 条
[1]   COMPUTER PROGRAM FOR FROST-SCHWEMER KINETICS EQUATIONS AND DERIVED TABLES [J].
BURKHARD, CA .
INDUSTRIAL AND ENGINEERING CHEMISTRY, 1960, 52 (08) :678-678
[2]  
Conibear A. C, 2010, THESIS RHODES U
[3]   THE KINETICS OF COMPETITIVE CONSECUTIVE 2ND-ORDER REACTIONS - THE SAPONIFICATION OF ETHYL ADIPATE AND OF ETHYL SUCCINATE [J].
FROST, AA ;
SCHWEMER, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (05) :1268-1273
[4]   Towards new antimalarial drugs: Synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors [J].
Giessmann, Dirk ;
Heidler, Philipp ;
Haemers, Timothy ;
Van Calenbergh, Serge ;
Reichenberg, Armin ;
Jomaa, Hassan ;
Weidemeyerd, Claus ;
Sanderbrand, Silke ;
Wiesner, Jochen ;
Link, Andreas .
CHEMISTRY & BIODIVERSITY, 2008, 5 (04) :643-656
[5]   Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs [J].
Jomaa, H ;
Wiesner, J ;
Sanderbrand, S ;
Altincicek, B ;
Weidemeyer, C ;
Hintz, M ;
Türbachova, I ;
Eberl, M ;
Zeidler, J ;
Lichtenthaler, HK ;
Soldati, D ;
Beck, E .
SCIENCE, 1999, 285 (5433) :1573-1576
[6]   BENZODIAZEPINE ANALOGS .9. KINETICS AND MECHANISM OF THE AZIDOTRIMETHYLSILANE-MEDIATED SCHMIDT REACTION OF FLAVANONES [J].
KAYE, PT ;
MPHAHLELE, MJ ;
BROWN, ME .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04) :835-838
[7]  
KEUSCH P, CHEM KINETICS RATE L
[8]   Microwave-assisted cleavage of phosphate, phosphonate and phosphoramide esters [J].
Kumar, G. D. Kishore ;
Saenz, David ;
Lokesh, G. L. ;
Natarajan, Amarnath .
TETRAHEDRON LETTERS, 2006, 47 (35) :6281-6284
[9]   THE DEVELOPMENT OF TRANSITION-STATE THEORY [J].
LAIDLER, KJ ;
KING, MC .
JOURNAL OF PHYSICAL CHEMISTRY, 1983, 87 (15) :2657-2664
[10]  
McKenna C.E., 1977, TETRAHEDRON LETT, V18, P155, DOI [10.1016/S0040-4039(01)92575-4, DOI 10.1016/S0040-4039(01)92575-4]