Aromatic sulfonation, 130: Relative intramolecular reactivity of the insulated π double bond and the 14π annulene perimeter toward Sulfur trioxide in the sulfonation of isopyrenes

Liebigs Annales

Volumn , Issue 1, 1997, Pages 49-53

  Cerfontain, Hans ^a   Bakker, Bert H ^a   Koeberg Telder, Ankie ^a   Wilmes, Oswald ^b,c  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF COLOGNE   (Germany)

^c BAYER AG   (Germany)

Author keywords

Sulfur trioxide sulfonation; 14 Annulene; 14 Annulenemono and disulfonic acids; Sultone and carbyl sulfate (pyrosultone) formation

Indexed keywords

EID: 0344324633     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970110     Document Type: Article

References (50)

1. C. M. Suter, B. P. Evans, J. M. Kiefer, J. Am. Chem. Soc. 1938, 60, 538-540.
2. K. K. Kelly, J. C. Matthews, J. Org. Chem. 1971, 36, 2159-2161.
3. K. Takei, K. Tsuto, S. Miyamoto, J. Wakatsuki, J. Am. Oil Chem. Soc. 1985, 62, 341-347.
4. R. M. Schonk, B. H. Bakker, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1992, 111, 389-401.
5. M. Nagayama, O. Okumura, S. Noda, H. Mandai, A. Mori, Bull. Chem. Soc. Jpn. 1974, 47, 2158-2161.
6. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1987, 28, 1699-1702, 1703-1706;
7. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1989, 30, 5451-5453.
8. D. S. Breslow, R. R. Hough, J. Am. Chem. Soc. 1957, 79, 5000-5002.
9. J. C. Sheehan, U. Zoller, J. Org. Chem. 1975, 40, 1179.
10. G. H. Weinreich, M. Jufresa, Bull. Soc. Chim. Fr. 1965, 787-794.
11. D. C. England, M. A. Dietrich, R. V. Lindsay, J. Am. Chem. Soc. 1960, 82, 6181-6188.
12. I. L. Knunyants, G. A. Sokolski, Angew. Chem. 1972, 84, 623-635;
13. Angew. Chem. Int. Ed. Engl. 1972, 11, 583-595.
14. R G. Bordwell, M. L. Peterson, C. S. Rondestvedt, J. Am. Chem. Soc. 1954, 76, 3945-3950.
15. J. L. Boyer, B. Gilot, J. P. Canselier, Phosphorus, Sulfur, Silicon 1984, 20, 259-271.
16. H. Cerfortain, A. Koeberg-Telder, H. J. A. Lambrechts, W. Lindner, S.-Z. Zhang, E. Vogel, J. Org. Chem. 1987, 52, 3373-3378.
17. [16].
18. K. Lammertsma, J. Am. Chem. Soc. 1982, 104, 2070-2072.
19. C. Kabuto, K. Fujimoro, M. Yasunami, K. Takase, N. Morita, T. Asao, Acta Crystallogr., Sect. C 1983, 39, 1245-1248.
20. E. Vogel, H. Wieland, L. Schmalstieg, J. Lex, Angew. Chem. 1984, 96, 717-719.
21. K. Müllen, H. Reel, Helv. Chim. Acta 1973, 56, 363-368;
22. J. Kolc, J. Michl, E. Vogel, J. Am. Chem. Soc. 1976, 98, 3935-3948;
23. C. Batich, E. Heilbronner, E. Vogel, Helv. Chim. Acta 1974, 57, 2288-2306.
24. [21].
25. H. C. Allen, E. K. Plyer, J. Am. Chem. Soc. 1958, 80, 2673-2676.
26. E. R. Hanna, K. T. Finley, W. H. Saunders, V. Boekelheide, J. Am. Chem. Soc. 1960, 82, 6342-6347;
27. A. Rosowsky, H. Fleischer, S. T. Young, R. Partch, W. H. Saunders, V. Boekelheide, Tetrahedron 1960, 11, 121-124.
28. E. Vogel, L. Schmalstieg, H.-J. Weyer, R. Gleiter, Chem. Lett. 1987, 33-36.
29. H. Reel, E. Vogel, Angew. Chem. 1972, 84, 1064-1066;
30. Angew. Chem. Int. Ed. Engl. 1972, 11, 1013-1014.
31. L. Schmalstieg, Doctorate Thesis (in German), Universität Köln, 1987.
32. O. Wilmes, Doctorate Thesis (in German), Universität Köln, 1990, p. 14.
33. R. Brause, Doctorate Thesis (in German), Universität Köln, 1990, p. 11-14.
34. H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1985, 104, 153-165.
35. H. Cerfontain, A. Koeberg-Telder, Recl. Trav. Chim. Pays-Bas 1970, 89, 569-574.
36. H. Cerfontain, A. Koeberg-Telder, K. Laali, H. J. A. Lambrechts, J. Org. Chem. 1982, 47, 4069-4075.
37. H. Cerfontain, A. Koeberg-Telder, C. Kruk, C. Ris, Anal. Chim. 1974, 46, 72-75.
38. G. M. Wallraff, E. Vogel, J. Michl, J. Org. Chem. 1988, 53, 5807-5812.
39. Note that the skeleton numbering of the products 4-7 differs from that of 5,10-dimethylisopyrene (3), from which they are formed!
40. [23].
41. B. H. Bakker, R. M. Schonk, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1990, 109, 485-486.
42. B. H. Bakker, R. M. Schonk, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1992, 111, 188-191.
43. [36].
44. D. W. Roberts, P. S. Jackson, C. D. Saul, C. J. Clement, Tetrahedron Lett. 1987, 28, 3383-3386.
45. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1989, 30, 5451-5454.
46. P. de Wit, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1985, 104, 25-36.
47. [24].
48. K. Nagayama, A. Kumar, K. Wuthrich, R. R. Ernst, J. Magn. Reson. 1980, 49, 321-334.
49. L. D. Hall, J. K. M. Sanders, J. Am. Chem. Soc. 1980, 102, 5703-5711.
50. R. Freeman, G. A. Morris, Bull. Magn. Reson. 1979, 1, 5-26.