Repetitive construction of macrocyclic oligophenylenes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 23, 1997, Pages 2654-2656

  Hensel, Volker ^a   Lützow, Karola ^a   Jacob, Joel ^a   Gessler, Katrin ^a   Saenger, Wolfram ^a   Schlüter, Arnulf Dieter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Cross coupling; Hydrocarbons; Hydrogen bonds; Macrocycles; Repetitive synthesis

Indexed keywords

EID: 0031573967     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199726541     Document Type: Article

References (46)

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27. For a definition of the term "module", see P. Kaszynski, A. C. Riedli, J. Michl, J. Am. Chem. Soc. 1992 114, 601; A.-D. Schlütcr, V. Hensel, P. Licss, K. Lützow, "Towards Oligophenylene Cycles and Related Structures: A Repetitive Approach" in Modular Chemistry (Ed.: J. Michl), NATO Series, Kluwcr, Dordrecht, The Netherlands, 1997, in press.
28. For a definition of the term "module", see P. Kaszynski, A. C. Riedli, J. Michl, J. Am. Chem. Soc. 1992 114, 601; A.-D. Schlütcr, V. Hensel, P. Licss, K. Lützow, "Towards Oligophenylene Cycles and Related Structures: A Repetitive Approach" in Modular Chemistry (Ed.: J. Michl), NATO Series, Kluwcr, Dordrecht, The Netherlands, 1997, in press.
29. 2)= 14.4, 23.0, 29.8, 32.0, 32.1, 33.3, 128.1, 128.2, 131.0, 131.4, 138.1, 141.3, 142.3. The NMR spectra show no indication of conformational isomers at room temperature. MS (El, 70 eV) mlz = 1922 (sample temperature 380C).
30. K. Lützow, V. Hensel, A.-D. Schlüter, unpublished results.
31. For a discussion of factors influencing ring formation, see G. Illuminati, L. Mandolini, Acc. Chem. Res. 1981, 14, 95.
32. 2 (conc); temperature: 85-150 C; scale: 50-1000 mg of module; reaction time: 12-96h.
33. Cycle la was prepared only from 6a and 7a.
34. Cycle la was also prepared from commercially available 1,3-diiodobenzenc and 6 a in 15% yield.
35. H. G. Kuivila, J. F. Reuwer, Jr., J. A. Mangravite, Can. J. Chem. 1963, 41, 3081.
36. 2 substitution pattern gives rise to polymers of high molecular weight [5a]. These polycondensations are carried out in concentrated solutions in which deboronification cannot effectively compete with crosscoupling.
37. Crystal structure of cyclic hexaphenylene: H. Irngartinger, L. Letserowitz, G. M. J. Schmidt, Chem. Ber. 1970, 103, 1132.
38. f can be explained by the presence of eight hexyl chains. Two of these chains (one on every molecule) are not included in the model, since they have a high disorder which could not be resolved in the difference Fourier maps. A. Altomare, G. Cascarano, C Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Ciyslallogr. 1994, 27, 435. G. M. Sheldrick, SHELXL76 Program for Crystal Simcture Determination, University of Cambridge, UK, 1976.
39. f can be explained by the presence of eight hexyl chains. Two of these chains (one on every molecule) are not included in the model, since they have a high disorder which could not be resolved in the difference Fourier maps. A. Altomare, G. Cascarano, C Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Ciyslallogr. 1994, 27, 435. G. M. Sheldrick, SHELXL76 Program for Crystal Simcture Determination, University of Cambridge, UK, 1976.
40. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-100529. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ (fax: int. code + (1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
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