A switchable hybrid [2]-catenane based on transition metal complexation and π-electron donor-acceptor interactions

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3905-3913

  Amabilino, David B ^a   Dietrich Buchecker, Christiane O ^a   Livoreil, Aude ^a   Pérez García, Lluïsa ^b   Sauvage, Jean Pierre ^a   Stoddart, J Fraser ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029946197     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954329+     Document Type: Article

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40. This threaded complex can be regarded as a precatenate (see ref 9) as well as a precursor to a family of rotaxanes. The reaction of suitably large stopper groups bearing chloro- or bromomethyl groups with the "precatenate" would afford rotaxanes. For examples of this kind of approach to rotaxanes, see: (a) Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1992, 1124-1128. For a more recent account with references. see. (b) Amabilino, D. B.; Ashton, P. R.; Bélohradsky, M., Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 751-753.
41. This threaded complex can be regarded as a precatenate (see ref 9) as well as a precursor to a family of rotaxanes. The reaction of suitably large stopper groups bearing chloro- or bromomethyl groups with the "precatenate" would afford rotaxanes. For examples of this kind of approach to rotaxanes, see: (a) Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1992, 1124-1128. For a more recent account with references. see. (b) Amabilino, D. B.; Ashton, P. R.; Bélohradsky, M., Raymo, F. M.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1995, 751-753.
42. Electrospray mass spectrometry has been used for the characterization of both families of catenanes from which the 'hybrid' catenane is derived as well as related copper(I) complexes, see: (a) Ashion, P. R.; Brown, C. L.; Chapman, J. R.; Gallagher, R. T.; Stoddart, J. F. Tetrahedron Lett. 1992, 33, 7771-7774. (b) Bitsch, F.; Dietrich-Buchecker, C.; Khémiss, A. K.; Sauvage, J.-P.; van Dorsselaer, J. Am. Chem. Soc. 1991, 113 , 4023-4025; A. Bitsch, F.: Hegy, G.; Dietrich-Buchecker, C.; Leize, E.; Sauvage, J.-P.; van Dorsselaer, A. New J. Chem. 1994, 18, 801-807. (c) Moucheron, C.; Dietrich-Buchecker. C. O.; Sauvage, J.-P.; van Dorsselaer, A. J. Chem. Soc., Dalton Trans. 1994, 885-893.
43. Electrospray mass spectrometry has been used for the characterization of both families of catenanes from which the 'hybrid' catenane is derived as well as related copper(I) complexes, see: (a) Ashion, P. R.; Brown, C. L.; Chapman, J. R.; Gallagher, R. T.; Stoddart, J. F. Tetrahedron Lett. 1992, 33, 7771-7774. (b) Bitsch, F.; Dietrich-Buchecker, C.; Khémiss, A. K.; Sauvage, J.-P.; van Dorsselaer, J. Am. Chem. Soc. 1991, 113 , 4023-4025; A. Bitsch, F.: Hegy, G.; Dietrich-Buchecker, C.; Leize, E.; Sauvage, J.-P.; van Dorsselaer, A. New J. Chem. 1994, 18, 801-807. (c) Moucheron, C.; Dietrich-Buchecker. C. O.; Sauvage, J.-P.; van Dorsselaer, A. J. Chem. Soc., Dalton Trans. 1994, 885-893.
44. Electrospray mass spectrometry has been used for the characterization of both families of catenanes from which the 'hybrid' catenane is derived as well as related copper(I) complexes, see: (a) Ashion, P. R.; Brown, C. L.; Chapman, J. R.; Gallagher, R. T.; Stoddart, J. F. Tetrahedron Lett. 1992, 33, 7771-7774. (b) Bitsch, F.; Dietrich-Buchecker, C.; Khémiss, A. K.; Sauvage, J.-P.; van Dorsselaer, J. Am. Chem. Soc. 1991, 113 , 4023-4025; A. Bitsch, F.: Hegy, G.; Dietrich-Buchecker, C.; Leize, E.; Sauvage, J.-P.; van Dorsselaer, A. New J. Chem. 1994, 18, 801-807. (c) Moucheron, C.; Dietrich-Buchecker. C. O.; Sauvage, J.-P.; van Dorsselaer, A. J. Chem. Soc., Dalton Trans. 1994, 885-893.
45. Electrospray mass spectrometry has been used for the characterization of both families of catenanes from which the 'hybrid' catenane is derived as well as related copper(I) complexes, see: (a) Ashion, P. R.; Brown, C. L.; Chapman, J. R.; Gallagher, R. T.; Stoddart, J. F. Tetrahedron Lett. 1992, 33, 7771-7774. (b) Bitsch, F.; Dietrich-Buchecker, C.; Khémiss, A. K.; Sauvage, J.-P.; van Dorsselaer, J. Am. Chem. Soc. 1991, 113 , 4023-4025; A. Bitsch, F.: Hegy, G.; Dietrich-Buchecker, C.; Leize, E.; Sauvage, J.-P.; van Dorsselaer, A. New J. Chem. 1994, 18, 801-807. (c) Moucheron, C.; Dietrich-Buchecker. C. O.; Sauvage, J.-P.; van Dorsselaer, A. J. Chem. Soc., Dalton Trans. 1994, 885-893.
46. Peaks from the free thread and copper complex of the macrocycle as a result of partial decomposition of the complex during the mass spectroscopic experiment, were also observed.
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49. The characteristics of the mass spectra of catenanes - in which the interlocked structure gives a peak, and then there is a "esert" in the spectrum until the component rings are observed - were first noted in the following seminal publications: (a) Vetter, W.; Schill, G. Tetrahedron 1967, 23, 3079-3093. (b) Vetter, W.; Loaemann, E.; Schill, G. Org. Mass. Spectrom. 1977, 12, 351-369.
50. The characteristics of the mass spectra of catenanes - in which the interlocked structure gives a peak, and then there is a "esert" in the spectrum until the component rings are observed - were first noted in the following seminal publications: (a) Vetter, W.; Schill, G. Tetrahedron 1967, 23, 3079-3093. (b) Vetter, W.; Loaemann, E.; Schill, G. Org. Mass. Spectrom. 1977, 12, 351-369.
51. 6 is treated with KCN in aqueous acetone, decomposition of the resulting catenand - specifically the tetracationic cyclophane component - means that the only isolable compound is the component neutral macrocycle. The decomposition is presumably a result of nucleophilic attack of the cyanide ion at the methylene groups adjacent to the quaternary nitrogen atom in the bipyridinium unit.
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