Formation of huge cyclic oligomers in the condensation polymerization of bis(9-hydroxy-1,4,7-trioxanonyl) substituted naphthalene and benzenes with both aromatic and aliphatic bis-acid chlorides

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1998, Pages 725-736

  Mertens, Ingrid J A ^a   Wegh, René ^a   Jenneskens, Leonardus W ^a   Vlietstra, Edward J ^a   Van Der Kerk van Hoof, Anca ^b   Zwikker, Jan W ^a   Cleij, Thomas J ^a   Smeets, Wilberth J J ^b   Veldman, Nora ^b   Spek, Anthony L ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347807622     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701920c     Document Type: Article

References (42)

1. M. Ballauf, Makromol. Chem., Rapid Commun., 1986, 7, 409.
2. V. Percec, C. Pugh, O. Nuyken and S. D. Pask, in Comprehensive Polymer Science, ed. G. Allen and J. C. Bevington, Pergamon Press, Oxford, 1989, vol. 6, p. 281.
3. R. Hilgenfeld and W. Saenger, Topics Curr. Chem., 1982, 101, 1; F. Vögtle, Supramolekulare Chemie, B. G. Teubner, Stuttgart, 1989; B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Compounds Chemistry, VCH Thieme, Weinheim, 1992.
4. R. Hilgenfeld and W. Saenger, Topics Curr. Chem., 1982, 101, 1; F. Vögtle, Supramolekulare Chemie, B. G. Teubner, Stuttgart, 1989; B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Compounds Chemistry, VCH Thieme, Weinheim, 1992.
5. R. Hilgenfeld and W. Saenger, Topics Curr. Chem., 1982, 101, 1; F. Vögtle, Supramolekulare Chemie, B. G. Teubner, Stuttgart, 1989; B. Dietrich, P. Viout and J.-M. Lehn, Macrocyclic Compounds Chemistry, VCH Thieme, Weinheim, 1992.
6. F. Vögtle, S. Meier and R. Hoss, Angew. Chem., Int. Ed. Engl., 1992, 31, 1619 and references cited therein.
7. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
8. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
9. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
10. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
11. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
12. H. M. Colquhoun, C. C. Dudman, M. Thomas, C. A. O'Mahony and D. J. Williams, J. Chem. Soc., Chem. Commun., 1990, 336; V. Percec, M. Kawasumi, P. L. Rinaldi, V. E. Litman, Macromolecules, 1992, 25, 3851; W. Memeger, J. Lazar, Jr., D. Ovenall, A. J. Arduengo and R. A. Leach, Macromol. Symp., 1994, 77, 105; D. J. Brunelle, H. O. Krabbenhoft and D. K. Bonauto, Macromol. Symp., 1994, 77, 117; B. R. Wood, J A. Semleyn and P. Hodge, Polymer, 1994, 35, 1542; M. Rothe, M. Lohmüller, U. Breuksch and G. Schmidtberg, Angew. Chem., Int. Ed. Engt., 1994, 33, 1960 and references cited therein.
13. F. J. Carver, C. A. Hunter and R. J. Shannon, J. Chem. Soc., Chem. Commun., 1994, 1277.
14. T. Ogawa, A. Yoshikawa, H. Wada, C. Ogawa, N. Ono and H. Suzuki, J. Chem. Soc., Chem. Commun., 1995, 1407.
15. B. H. Kim, E. J. Jeong and W. H. June, J. Am. Chem. Soc., 1995, 117, 6390.
16. S. Inokuma, S. Sakai and J. Nishimura, Top. Curr. Chem., 1994, 172, 87 and references cited therein.
17. For 3a(n) with n = 1-5 preliminary communication: I. J. A. Mertens, L. W. Jenneskens, E. J. Vlietstra, A. C. Van der Kerk-van Hoof, J. W. Zwikker, W. J. J. Smeets and A. L. Spek, J. Chem. Soc., Chem. Commun., 1995, 1621 and references cited therein.
18. D. A. Jaeger and R. R. Whitney, J. Org. Chem., 1975, 40, 92.
19. R. T. Gray, D. N. Reinhoudt, K. Spaargaren and J. F. De Bruijn, J. Chem. Soc., Perkin Trans. 2, 1977, 206.
20. N. J. Turro, Modern Molecular Photochemistry, Benjamin/ Cummings, London, 1978.
21. WIN-NMR Bruker Spectrospin AG Fällanden, Switzerland, 1990; P. Budzelaar, GeNMR (version 3.51), IvorySoft, Amsterdam, The Netherlands, 1994.
22. WIN-NMR Bruker Spectrospin AG Fällanden, Switzerland, 1990; P. Budzelaar, GeNMR (version 3.51), IvorySoft, Amsterdam, The Netherlands, 1994.
23. R. Abraham and G. Gatti, J. Chem. Soc. B, 1969, 961; L. Philips and V. Wray, J. Chem. Soc., Perkin Trans. 2, 1972, 536 and references cited therein; J. Dale, Tetrahedron, 1974, 30, 1683; E. Riande, M. Jimeno, R. Salvador, J. De Abajo and J. Guzman, J. Phys. Chem., 1990, 94, 7435.
24. R. Abraham and G. Gatti, J. Chem. Soc. B, 1969, 961; L. Philips and V. Wray, J. Chem. Soc., Perkin Trans. 2, 1972, 536 and references cited therein; J. Dale, Tetrahedron, 1974, 30, 1683; E. Riande, M. Jimeno, R. Salvador, J. De Abajo and J. Guzman, J. Phys. Chem., 1990, 94, 7435.
25. R. Abraham and G. Gatti, J. Chem. Soc. B, 1969, 961; L. Philips and V. Wray, J. Chem. Soc., Perkin Trans. 2, 1972, 536 and references cited therein; J. Dale, Tetrahedron, 1974, 30, 1683; E. Riande, M. Jimeno, R. Salvador, J. De Abajo and J. Guzman, J. Phys. Chem., 1990, 94, 7435.
26. R. Abraham and G. Gatti, J. Chem. Soc. B, 1969, 961; L. Philips and V. Wray, J. Chem. Soc., Perkin Trans. 2, 1972, 536 and references cited therein; J. Dale, Tetrahedron, 1974, 30, 1683; E. Riande, M. Jimeno, R. Salvador, J. De Abajo and J. Guzman, J. Phys. Chem., 1990, 94, 7435.
27. MMX force field as implemented in PCMODEL 4.0, Serena Software, Bloomington, IN, USA, 1990; AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc, 1985, 107, 3902; MOPAC 7.0: J. J. P. Stewart, 1993.
28. MMX force field as implemented in PCMODEL 4.0, Serena Software, Bloomington, IN, USA, 1990; AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc, 1985, 107, 3902; MOPAC 7.0: J. J. P. Stewart, 1993.
29. MMX force field as implemented in PCMODEL 4.0, Serena Software, Bloomington, IN, USA, 1990; AM1: M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc, 1985, 107, 3902; MOPAC 7.0: J. J. P. Stewart, 1993.
30. CRC Handbook of Chemistry and Physics, ed. D. R. Lide, CRC Press, Boca Raton, 76th edn., 1995-1996.
31. J. Liptay and W. Liptay, Z. Naturforsch., Teil A, 1960, 20a, 1441.
32. J. March, Advanced Organic Chemistry, Reactions, Mechanisms and Structure, Wiley, New York, 4th edn., 1992.
33. D. B. Amabilino and J. F. Stoddart, Chem. Rev., 1995, 95, 2725 and references cited therein; P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31 and references cited therein.
34. D. B. Amabilino and J. F. Stoddart, Chem. Rev., 1995, 95, 2725 and references cited therein; P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31 and references cited therein.
35. C. A. Hunter, Chem. Soc. Rev., 1994, 101 and references cited therein.
36. I. J. A. Mertens, J. E. M. J. Raaymakers, L. W. Jenneskens and A. L. Spek, QCPE Bulletin, 1995, 15, 30.
37. E. Weber, J. L. Toner, I. Goldberg, F. Vögtle, D. A. Laidler, J. F. Stoddart, R. A. Bartsch and C. L. Liotta, in Crown Ethers and Analogs, ed. S. Patai and Z. Rappoport, Wiley, Chichester, 1989, p. 402.
38. G. M. Sheldrick, SHELXS-86. Program for crystal structure determination, Univ. of Göttingen, Federal Republic of Germany, 1986.
39. G. M. Sheldrick, SHELXL-93. Program for crystal structure refinement, Univ. of Göttingen, Federal Republic of Germany, 1993.
40. S. Shinkai, K. Inuzuka, O. Miyazaki and O. Manabe, J. Am. Chem. Soc., 1985, 107, 3950.
41. P. L. Anelli, P. R. Ashton, N. Spencer, A. M. Z. Slawin, J. Fraser Stoddart and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1991, 30, 1036.
42. M. J. Gunter, D. C. R. Hockless, M. R. Johnston, B. W. Skelton and A. H. White, J. Am. Chem. Soc., 1994, 116, 4810.