1H NMR-based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative

被引：1
|
作者：
Lobb, Kevin A. [1 ]
Kaye, Perry T. [1 ]
机构：
[1] Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
来源：
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 2011年 / 24卷 / 01期
基金：
新加坡国家研究基金会;
关键词：
mechanistic study; skeletal rearrangements; spirobornyl tosylate; RACEMIZATION;
D O I：
10.1002/poc.1699
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
H-1 NMR analysis of the kinetics of skeletal rearrangement of optically pure 3,3-xylyl-2-exo-bornyl tosylate in CDCl3 indicates the operation of tandem autocatalytic and pseudo-first-order transformations, leading sequentially to a pair of isomeric camphene derivatives and involving partial racemization. Changing the solvent system has been shown to permit the chemoselective isolation of either of the isomeric camphenes. Copyright (C) 2010 John Wiley & Sons, Ltd.
引用
收藏
页码：38 / 44
页数：7
相关论文
共 50 条
  • [1] 1H NMR-based metabolomic study of metabolic profiling for pollinosis
    Zhou, Yan-jun
    Li, Li-Sha
    Sun, Jin-Lu
    Guan, Kai
    Wei, Ji-Fu
    WORLD ALLERGY ORGANIZATION JOURNAL, 2019, 12 (01):
  • [2] 1H NMR-based metabolomics and lipidomics of microalgae
    Nanda, Manisha
    Kumar, Vinod
    Arora, Neha
    Vlaskin, Mikhail S.
    Tripathi, Manoj K.
    TRENDS IN PLANT SCIENCE, 2021, 26 (09) : 984 - 985
  • [3] A 1H NMR-based Metabolomics Approach for Mechanistic Insight into Acetaminophen-induced Hepatotoxicity
    Fukuhara, Kiyoshi
    Ohno, Akiko
    Ando, Yosuke
    Yamoto, Takashi
    Okuda, Haruhiro
    DRUG METABOLISM AND PHARMACOKINETICS, 2011, 26 (04) : 399 - 406
  • [4] 1H NMR-based metabonomics for investigating diabetes
    Maher, Anthony D.
    Lindon, John C.
    Nicholson, Jeremy K.
    FUTURE MEDICINAL CHEMISTRY, 2009, 1 (04) : 737 - 747
  • [5] Serum profiling of anorexia nervosa: A 1H NMR-based metabolomics study
    Salehi, Alireza M.
    Nilsson, Ida A. K.
    Figueirae, Joao
    Thornton, Laura M.
    Abdulkarim, Israa
    Palsson, Erik
    Bulik, Cynthia M.
    Landen, Mikael
    EUROPEAN NEUROPSYCHOPHARMACOLOGY, 2021, 49 : 1 - 10
  • [6] 1H NMR-Based Kinetic-Mechanistic Study of the Intramolecular Trans-esterification of 2-exo-3-exo-Dihydroxybornane Monoacrylate Esters
    Duggan, Andrew R.
    Mciteka, Lulama P.
    Lobb, Kevin A.
    Kaye, Perry T.
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2013, 66 : 140 - 144
  • [7] Analytical reproducibility in 1H NMR-based metabonomic urinalysis
    Keun, HC
    Ebbels, TMD
    Antti, H
    Bollard, ME
    Beckonert, O
    Schlotterbeck, G
    Senn, H
    Niederhauser, U
    Holmes, E
    Lindon, JC
    Nicholson, JK
    CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (11) : 1380 - 1386
  • [8] 1H NMR-based metabolite profiling for biomarker identification
    Silva, Ruan A.
    Pereira, Tayla C. S.
    Souza, Alzenir R.
    Ribeiro, Paulo R.
    CLINICA CHIMICA ACTA, 2020, 502 : 269 - 279
  • [9] 1H NMR-based metabolomic study of the effects of flavonoids on citrinin production by Monascus
    He, Shanshan
    Wang, Yanling
    Xie, Jianhua
    Gao, Heng
    Li, Xiujiang
    Huang, Zhibing
    FOOD RESEARCH INTERNATIONAL, 2020, 137
  • [10] 1H NMR-based metabolomic study of metabolic profiling for systemic lupus erythematosus
    Ouyang, X.
    Dai, Y.
    Wen, J. L.
    Wang, L. X.
    LUPUS, 2011, 20 (13) : 1411 - 1420
12345