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Volumn 3, Issue 3, 1997, Pages 463-481

Axially chiral catenanes and π-electron-deficient receptors

Author keywords

catenanes; chirality; enantio selection; receptors; self assembly

Indexed keywords


EID: 0031005173     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030319     Document Type: Article
Times cited : (51)

References (93)
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    • The intermolecular noncovalent bonds responsible for the self-assembly of the catenanes of the type described in this paper remain evident in the solution and solid-state structures of the interlocked molecular compounds. See: a) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399; b) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193-218; c) D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godinez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraskiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, ibid. 1995, 117, 1271-1293; d) P. R. Ashton, L. Pérez-García, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1995, 34, 571-574.
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    • The intermolecular noncovalent bonds responsible for the self-assembly of the catenanes of the type described in this paper remain evident in the solution and solid-state structures of the interlocked molecular compounds. See: a) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1989, 28, 1396-1399; b) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193-218; c) D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godinez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraskiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, ibid. 1995, 117, 1271-1293; d) P. R. Ashton, L. Pérez-García, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1995, 34, 571-574.
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    • A topologically chiral [2]catenane has been synthesized successfully by Sauvage and coworkers and resolved into its two enantiomers by chiral HPLC. See: a) J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, J. Am. Chem. Soc. 1992, 114, 4625-4631; b) Y. Kaida, Y. Okamoto, J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, Tetrahedron Lett. 1993, 34, 1019-1023.
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    • Chambron, J.-C.1    Mitchell, D.K.2    Sauvage, J.-P.3
  • 56
    • 0027499980 scopus 로고
    • A topologically chiral [2]catenane has been synthesized successfully by Sauvage and coworkers and resolved into its two enantiomers by chiral HPLC. See: a) J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, J. Am. Chem. Soc. 1992, 114, 4625-4631; b) Y. Kaida, Y. Okamoto, J.-C. Chambron, D. K. Mitchell, J.-P. Sauvage, Tetrahedron Lett. 1993, 34, 1019-1023.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1019-1023
    • Kaida, Y.1    Okamoto, Y.2    Chambron, J.-C.3    Mitchell, D.K.4    Sauvage, J.-P.5
  • 64
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    • The synthesis of this cyclophane has been already published by Hünig et al.; see a) M. Buhner, W. Geuder, W.-K. Gries, S. Hünig, M. Koch, T. Poll, Angew. Chem. Int. Ed. Engl. 1988, 27, 1553-1556, and for similar work: b) W. Geuder, S. Hünig, A. Suchy, Tetrahedron 1986, 42, 1665-1677.
    • (1986) Tetrahedron , vol.42 , pp. 1665-1677
    • Geuder, W.1    Hünig, S.2    Suchy, A.3
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    • The use of a ferrocene-based template has recently proved to be useful for the template-directed synthesis of cyclobis(paraquat-4.4′-biphenylene). See a) P. R. Ashton, S. Menzer, F. M. Raymo, G. K. H. Shimizu, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1996, 487-490; b) M. Asakawa, P. R. Ashton, S. Menzer, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 877-893.
    • (1996) J. Chem. Soc. Chem. Commun. , pp. 487-490
    • Ashton, P.R.1    Menzer, S.2    Raymo, F.M.3    Shimizu, G.K.H.4    Stoddart, J.F.5    Williams, D.J.6
  • 66
    • 0000597680 scopus 로고    scopus 로고
    • The use of a ferrocene-based template has recently proved to be useful for the template-directed synthesis of cyclobis(paraquat-4.4′-biphenylene). See a) P. R. Ashton, S. Menzer, F. M. Raymo, G. K. H. Shimizu, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1996, 487-490; b) M. Asakawa, P. R. Ashton, S. Menzer, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 877-893.
    • (1996) Chem. Eur. J. , vol.2 , pp. 877-893
    • Asakawa, M.1    Ashton, P.R.2    Menzer, S.3    Raymo, F.M.4    Stoddart, J.F.5    White, A.J.P.6    Williams, D.J.7
  • 70
    • 0343643243 scopus 로고    scopus 로고
    • note
    • Stability toward racemization has been tested for the model compound 2.2′-binaphthol. See ref. [24c].
  • 77
    • 0342772974 scopus 로고    scopus 로고
    • ref. [12c]
    • For a more detailed discussion about the "rocking" process - that is, the equilibrations of the protons attached to the included hydroquinone rings between positions where they are directed toward the center of the p-phenylene ring in the p-xylyl spacer of the cyclophane and positions where they protrude outside the π-electron-deficient cavity - see: a) ref. [12c]; b) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1063-1066.
  • 78
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    • For a more detailed discussion about the "rocking" process - that is, the equilibrations of the protons attached to the included hydroquinone rings between positions where they are directed toward the center of the p-phenylene ring in the p-xylyl spacer of the cyclophane and positions where they protrude outside the π-electron-deficient cavity - see: a) ref. [12c]; b) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, D. J. Williams, Synlett 1994, 1063-1066.
    • (1994) Synlett , pp. 1063-1066
    • Ashton, P.R.1    Preece, J.A.2    Stoddart, J.F.3    Tolley, M.S.4    Williams, D.J.5
  • 79
    • 85088675705 scopus 로고    scopus 로고
    • note
    • 2CO until no further precipitation occurred.
  • 81
    • 0343643241 scopus 로고    scopus 로고
    • See, for example, refs. [12] and [23]
    • See, for example, refs. [12] and [23].
  • 85
    • 0029117927 scopus 로고
    • and references cited therein
    • For a discussion on [CH ⋯ π] interactions, see: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665-8701 and references cited therein.
    • (1995) Tetrahedron , vol.51 , pp. 8665-8701
    • Nishio, M.1    Umezawa, Y.2    Hirota, M.3    Takeuchi, Y.4
  • 87
    • 0342772973 scopus 로고    scopus 로고
    • Spartan V 4.1. Wavefunction, 18401 Von Karman Ave., 370 Irvine CA 92715, USA
    • Spartan V 4.1. Wavefunction, 18401 Von Karman Ave., 370 Irvine CA 92715, USA.
  • 93
    • 0343643239 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100084. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: Int. code+(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.