Size-Selective Phase-Transfer Catalysis with Interfacially Cross-Linked Reverse Micelles

被引：19
作者：
Lee, Li-Chen [1 ]
Zhao, Yan [1 ]
机构：
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 03期
基金：
美国国家科学基金会;
关键词：
MOLECULAR RECOGNITION; CHEMISTRY; HEMICARCERAND; FOLDAMERS; FUTURE; STATE; ACID;
D O I：
10.1021/ol203319w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cross-linking of the reverse micelles (RMs) of a triallylammonium surfactant afforded organic nanoparticles with introverted cationic groups. The cross-linked reverse micelles catalyzed size-selective biphasic reaction between sodium azide and alkyl bromides. Size selectivity of up to 9:1 was obtained for alkyl bromides with similar structures. The selectivity was influenced strongly by the size of the water pool and proposed to happen as a result of the "sieving" effect of the alkyl corona.
引用
收藏
页码：784 / 787
页数：4
相关论文
共 22 条
  • [1] Molecular Recognition of a Transition State
    Bao, Xiaoguang
    Rieth, Stephen
    Stojanovic, Sandra
    Hadad, Christopher M.
    Badjic, Jovica D.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (28) : 4816 - 4819
  • [2] The Emergence of Thiol-Ene Coupling as a Click Process for Materials and Bioorganic Chemistry
    Dondoni, Alessandro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (47) : 8995 - 8997
  • [3] Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels
    Fiedler, D
    Leung, DH
    Bergman, RG
    Raymond, KN
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (04) : 349 - 358
  • [4] Crystal structures of the CP1 domain from Thermus thermophilus isoleucyl-tRNA synthetase and its complex with L-valine
    Fukunaga, R
    Fukai, S
    Ishitani, R
    Nureki, O
    Yokoyama, S
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (09) : 8396 - 8402
  • [5] Templation of the excited-state chemistry of (α-(n-alkyl) dibenzyl ketones:: How guest packing within a nanoscale supramolecular capsule influences photochemistry
    Gibb, Corinne L. D.
    Sundaresan, Arun Kumar
    Ramamurthy, V.
    Gibb, Bruce C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) : 4069 - 4080
  • [6] Thiol-enes: Chemistry of the past with promise for the future
    Hoyle, CE
    Lee, TY
    Roper, T
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (21) : 5301 - 5338
  • [7] Synthesis and characterization of cross-linked reverse micelles
    Jung, HM
    Price, KE
    McQuade, DT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) : 5351 - 5355
  • [8] Innermolecular Reactions of Fluorophenylcarbene inside a Hemicarcerand
    Lu, Zhifeng
    Moss, Robert A.
    Sauers, Ronald R.
    Warmuth, Ralf
    [J]. ORGANIC LETTERS, 2009, 11 (17) : 3866 - 3869
  • [9] Naphthalene Diels-Alder in a Self-Assembled Molecular Flask
    Murase, Takashi
    Horiuchi, Shinnosuke
    Fujita, Makoto
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2866 - +
  • [10] Pileni M.P., 1989, STRUCTURE REACTIVITY
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