Magic ring catenation by olefin metathesis

被引:124
作者
Guidry, EN
Cantrill, SJ
Stoddart, JF
Grubbs, RH
机构
[1] Univ Calif Los Angeles, Calif NanoSyst Inst, Los Angeles, CA 90095 USA
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[3] CALTECH, Arnold & Mabel Beckman Lab Chem Synth, Pasadena, CA 91125 USA
关键词
D O I
10.1021/ol050463f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Olefin metathesis has been employed in the efficient syntheses of a [2]catenane with the templation being provided by the recognition between a secondary ammonium ion and a crown ether. In one approach, a crown ether precursor has been clipped around an NH2+ center situated in a macrocyclic ring, yielding the mechanically interlocked compound. In the other approach, the reversible nature of olefin metathesis allows for a magic ring synthesis to occur wherein two free macrocycles can be employed as the stationary materials, leading to the formation of the same [2]catenane.
引用
收藏
页码:2129 / 2132
页数:4
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共 60 条
  • [1] Interlocked and intertwined structures and superstructures
    Amabilino, DB
    Stoddart, JF
    [J]. CHEMICAL REVIEWS, 1995, 95 (08) : 2725 - 2828
  • [2] Synthesis of a [2]catenane around a Ru(diimine)32+ scaffold by ring-closing metathesis of olefins
    Arico, F
    Mobian, P
    Kern, JM
    Sauvage, JP
    [J]. ORGANIC LETTERS, 2003, 5 (11) : 1887 - 1890
  • [3] The exclusivity of multivalency in dynamic covalent processes
    Badjic, JD
    Cantrill, SJ
    Grubbs, RH
    Guidry, EN
    Orenes, R
    Stoddart, JF
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) : 3273 - 3278
  • [4] A molecular meccano kit
    Cantrill, SJ
    Pease, AR
    Stoddart, JF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (21): : 3715 - 3734
  • [5] Nanoscale borromean rings
    Cantrill, SJ
    Chichak, KS
    Peters, AJ
    Stoddart, JF
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (01) : 1 - 9
  • [6] Rotaxane formation under thermodynamic control
    Cantrill, SJ
    Rowan, SJ
    Stoddart, JF
    [J]. ORGANIC LETTERS, 1999, 1 (09) : 1363 - 1366
  • [7] DNA topoisomerases: Structure, function, and mechanism
    Champoux, JJ
    [J]. ANNUAL REVIEW OF BIOCHEMISTRY, 2001, 70 : 369 - 413
  • [8] Molecular Borromean rings
    Chichak, KS
    Cantrill, SJ
    Pease, AR
    Chiu, SH
    Cave, GWV
    Atwood, JL
    Stoddart, JF
    [J]. SCIENCE, 2004, 304 (5675) : 1308 - 1312
  • [9] Factors affecting the threading of axle molecules through macrocycles: Binding constants for semirotaxane formation
    Clifford, T
    Abushamleh, A
    Busch, DH
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) : 4830 - 4836
  • [10] A [2]catenane-based solid state electronically reconfigurable switch
    Collier, CP
    Mattersteig, G
    Wong, EW
    Luo, Y
    Beverly, K
    Sampaio, J
    Raymo, FM
    Stoddart, JF
    Heath, JR
    [J]. SCIENCE, 2000, 289 (5482) : 1172 - 1175