In situ kinetic studies of the trifluoromethylation of caffeine with Zn(SO2CF3)2

被引：15
|
作者：
Baxter, Ryan D. [1 ]
Blackmond, Donna G. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
TETRAHEDRON | 2013年 / 69卷 / 27-28期
关键词：
Trifluoromethylation; Kinetics; C-H functionalization; Reaction progress; Reaction mechanism; SUBSTITUTIONS; RADICALS;
D O I：
10.1016/j.tet.2013.04.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In situ monitoring of the trifluoromethylation of caffeine using Zn(SO2CF3)(2) provides mechanistic insight into this important reaction. The concentration dependences of each of the reagents are probed, along with the effect of various additives. The kinetic profile is characterized by a rapid initial regime followed by a period of slower rate. Increasing the concentration of the Zn reagent extends the initial rapid period to higher conversions. Neither the caffeine concentration nor the concentration of the oxidant has a strong effect on the reaction rate. A multiple aliquot method is introduced to help deconvolute factors associated with each rate regime. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5604 / 5608
页数：5
相关论文
共 50 条
  • [1] Studies of ENR-50 and LiN(SO2CF3)2 electrolyte system
    Zainal, Norazlin
    Idris, Razali
    Mohamed, Nor Sabirin
    ADVANCEMENT OF MATERIALS AND NANOTECHNOLOGY II, 2012, 545 : 303 - +
  • [2] Electrogeneration of polypyrrole films doped with LiN(SO2CF3)2
    Villareal, I
    Morales, E
    Otero, TF
    Acosta, JL
    SYNTHETIC METALS, 2000, 108 (01) : 57 - 65
  • [3] A NEW CYCLIC FLUORINATED TRISULFONE (CF2SO2)3 AND FLUORINATED DERIVATIVES - SO2(CF2SO2F)2, CF2(SO2CF3)2, CF3SO2CF2SO2F, CF2(SO2F)2 AND CF3SO2CF2SO2CF2SO2F
    WATERFELD, A
    WEISS, I
    OBERHAMMER, H
    GARD, GL
    MEWS, R
    JOURNAL OF FLUORINE CHEMISTRY, 1994, 67 (01) : 27 - 31
  • [4] Crystallographic Insight into the Mg2+ Coordination Mode and N(SO2CF3)2- Anion Conformation in Mg[N(SO2CF3)2]2 and Its Adducts
    Veryasov, Gleb
    Harinaga, Ukyo
    Matsumoto, Kazuhiko
    Hagiwara, Rika
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (07) : 1087 - 1099
  • [5] TRIS((TRIFLUOROMETHYL)SULFONYL)METHANE, HC(SO2CF3)3
    TUROWSKY, L
    SEPPELT, K
    INORGANIC CHEMISTRY, 1988, 27 (12) : 2135 - 2137
  • [6] PHOTOSUBSTITUTES OF SO2NH2, SO2CH3, AND SO2CF3 GROUPS IN BENZENE SERIES
    FROLOV, AN
    ELTSOV, AV
    KULBITSK.OV
    ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (02): : 432 - &
  • [7] Unique Behavior of Dimethoxyethane (DME)/Mg(N(SO2CF3)2)2 Solutions
    Salama, Michael
    Shterenberg, Ivgeni
    Gizbar, Haim
    Eliaz, Neta N.
    Kosa, Monica
    Keinan-Adamsky, Keren
    Afri, Michal
    Shimon, Linda J. W.
    Gottlieb, Hugo E.
    Major, Dan T.
    Gofer, Yosef
    Aurbach, Doron
    JOURNAL OF PHYSICAL CHEMISTRY C, 2016, 120 (35): : 19586 - 19594
  • [8] Synthesis of LiCH(SO2CF3)(2) and ionic conductivity of polyether salt complexes
    Holcomb, NR
    Nixon, PG
    Gard, GL
    Nafshun, RL
    Lerner, MM
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1996, 143 (04) : 1297 - 1300
  • [9] Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2•bPY
    Pan, Shitao
    Wang, Xiu
    Ni, Chuanfa
    Hu, Jinbo
    TETRAHEDRON, 2021, 100
  • [10] Comparative Study of M[N(SO2F)(SO2CF3)]-[N-Butyl-N-methylpyrroridinium][N(SO2F)(SO2CF3)] (M = Li, Na, K, Rb, Cs) Ionic Liquid Electrolytes
    Yamamoto, Takayuki
    Nishijima, Shu
    Nohira, Toshiyuki
    JOURNAL OF PHYSICAL CHEMISTRY B, 2020, 124 (38): : 8380 - 8387
12345