Thermal rearrangements of di- and triphenyl-substituted benzocyclobutenes and corresponding o-quinodimethanes

European Journal of Organic Chemistry

Volumn , Issue 3, 1999, Pages 551-563

  Paul, Thomas ^a   Boese, Roland ^a   Steller, Ingo ^a   Bandmann, Heinz ^a   Gescheidt, Georg ^b   Korth, Hans Gert ^a   Sustmann, Reiner ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

9 Anthryl radicals; Benzocyclobutenes; o Quinodimethanes; Pericyclic reactions; Retrodisproportionation

Indexed keywords

2 QUINODIMETHANE DERIVATIVE; 7 ISOCYANO 7,8,8 TRIPHENYLBENZOCYCLOBUTENE; 7 METHOXY 7,8,8 TRIPHENYLBENZOCYCLOBUTENE; 7 METHYL 7,8,8 TRIPHENYLBENZOCYCLOBUTENE; 7,7,8 TRIPHENYLBENZOCYCLOBUTENE; 7,8 DIMETHOXY 7,8 DIPHENYLBENZOCYCLOBUTENE; 7,8 DIMETHYL 7,8 DIPHENYLBENZOCYCLOBUTENE; FUSED ALICYCLIC AROMATIC COMPOUND; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SPECTROSCOPY; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

EID: 0032794535     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199903)1999:3<551::AID-EJOC551>3.0.CO;2-2     Document Type: Article

References (50)

1. [1a] J. J. McCullogh, Acc. Chem. Res. 1980, 13, 270-276.
2. [1b] C. W. G. Fishwick, D. W. Jones in The Chemistry of Quinoid Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, Chichester, 1988, pp. 403-453.
3. [1c] J. L. Charlton, M. M. Alauddin, Tetrahedron 1987, 43, 2873-2889.
4. R. B. Woodward, R. Hoffmann, Die Erhaltung der Orbitalsymmetrie, Akademische Verlagsgesellschaft Geest & Portig, Leipzig, 1970, p. 50; cf. Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
5. R. B. Woodward, R. Hoffmann, Die Erhaltung der Orbitalsymmetrie, Akademische Verlagsgesellschaft Geest & Portig, Leipzig, 1970, p. 50; cf. Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
6. R. B. Woodward, R. Hoffmann, Die Erhaltung der Orbitalsymmetrie, Akademische Verlagsgesellschaft Geest & Portig, Leipzig, 1970, p. 50; cf. Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781.
7. [3a] R. Huisgen, H. Seidel, Tetrahedron Lett. 1964, 3381-3384.
8. [3b] G. Quinkert, K. Opitz, W. W. Wiersdorff, M. Finke, Tetrahedron Lett. 1965, 3009-3013.
9. L. A. Carpino, J. Am. Chem. Soc. 1962, 84, 2196-2201.
10. W. R. Roth, V. Rekowski, S. Börner, M. Quast, Liebigs Ann. 1996, 409-430.
11. T. Paul, M. A. Hassan,. D. V. Avila, H.-G. Korth, R. Sustmann, J. Org. Chem. 1996, 61, 6835-6848.
12. [7a] H.-G. Korth, K. U. Ingold, R. Sustmann, H. de Groot, H. Sies, Angew. Chem. 1992, 107, 915-917; Angew. Chem. Int. Ed. Engl. 1992, 31, 891-893.
13. [7a] H.-G. Korth, K. U. Ingold, R. Sustmann, H. de Groot, H. Sies, Angew. Chem. 1992, 107, 915-917; Angew. Chem. Int. Ed. Engl. 1992, 31, 891-893.
14. [7b] H.-G. Korth, R. Sustmann, P. Lommes, T. Paul, A. Ernst, H. de Groot, L. Hughes, K. U. Ingold, J. Am. Chem. Soc. 1994, 116, 2767-2777.
15. [8a] G. Quinkert, Pure Appl. Chem. 1964, 9, 607-621.
16. [8b] K. H. Grellmann, J. Palmowski, G. Quinkert, Angew. Chem. 1971, 83, 209-210; Angew. Chem. Int. Ed. Engl. 1971, 10, 196-197.
17. [8b]K. H. Grellmann, J. Palmowski, G. Quinkert, Angew. Chem. 1971, 83, 209-210; Angew. Chem. Int. Ed. Engl. 1971, 10, 196-197.
18. [8c]G. Quinkert, J. Palmowski, H. P. Lorenz, W. W. Wiersdorff, M. Finke, Angew. Chem. 1971, 83, 210-212; Angew. Chem. Int. Ed. Engl. 1971, 10, 197-198.
19. [8c] G. Quinkert, J. Palmowski, H. P. Lorenz, W. W. Wiersdorff, M. Finke, Angew. Chem. 1971, 83, 210-212; Angew. Chem. Int. Ed. Engl. 1971, 10, 197-198.
20. [8d] G. Quinkert, W. W. Wiersdorff, M. Finke, K. Opitz, F.-G. von der Haar, Chem. Ber. 1968, 101, 2302-2325.
21. [8e] K. K. de Fonseka, J. J. McCullough, A. J. Yarwood, J. Am. Chem. Soc. 1979, 101, 3277-3282.
22. [8f] V. Wintgens, J. C. Netto-Ferreira, H. L. Casal, J. C. Scaiano, J. Am. Chem. Soc. 1990, 112, 2363-2367.
23. [8g] R. W. Redmond, C. W. Harwig, J. C. Scaiano, Photochem. Photobiol. A 1992, 68, 255-259.
24. [8h] J. C. Netto-Ferreira, V. Wintgens, J. C. Scaiano, Tetrahedron Lett. 1989, 30, 6851-6854.
25. [8i] J. C. Scaiano, V. Wintgens, J. C. Netto-Ferreira, Pure Appl. Chem. 1990, 62, 1557-1564.
26. [8j] D. W. Jones, G. Kneen, J. Chem. Soc., Perkin Trans. 1 1975, 171-174.
27. [8k] J. M. Holland, D. W. Jones, J. Chem. Soc. (C) 1971, 608-612.
28. CKS, Chemical Kinetics Simulator, v. 1.02, IBM Almaden Research Center, Almaden, 1995.
29. W. R. Roth, T. Ebbrecht, A. Beitat, Chem. Ber. 1988, 121, 1357-1358.
30. H. Kropf, S. Munke, in Methoden der Organischen Chemie (Houben-Weyl), vol. E13/2, 4th Ed., Thieme, Stuttgart, 1988, p. 1388.
31. [12a] J. Rigaudy, G. Chelu, N. K. Cuong, J. Org. Chem. 1985, 50, 4474-4478.
32. [12b] F. Gobert, S. Combrisson, Tetrahedron 1974, 30, 2919-2924.
33. [12c] M. Oyama, K. Nozaki, S. Okazagi, J. Electroanal. Chem. 1991, 304, 61-73.
34. J. Wisniak, M. Herskowitz, Solubility of Gases and Solids, Part B, Physical Sciences Data 18, Elsevier, Amsterdam, 1984.
35. F. Wilkinson, Pure Appl. Chem. 1997, 69, 851-856.
36. [15a] G. Porter, M. F. Tchir, J. Chem. Soc. (A) 1970, 1372-1373.
37. [15b] G. Porter, M. F. Tchir, J. Chem. Soc., Chem. Commun. 1971, 3772-3777.
38. [15c] G. Quinkert, H.-P. Lorenz, W. W. Wiersdorff, Chem. Ber. 1969, 102, 1597-1605.
39. C. Rüchardt, M. Gerst, J. Ebenhoch, Angew. Chem. 1997, 109, 1474-1498; Angew. Chem. Int. Ed. Engl. 1997, 36, 1406-1430.
40. C. Rüchardt, M. Gerst, J. Ebenhoch, Angew. Chem. 1997, 109, 1474-1498; Angew. Chem. Int. Ed. Engl. 1997, 36, 1406-1430.
41. H. H. Perkampus, UV-Vis Atlas of Organic Compounds, Part 2, 2nd ed., VCH, Weinheim, 1992, p. 622.
42. [18a] R. Boese, D. Bläser, Angew. Chem. 1988, 100, 293-295; Angew. Chem. Int. Ed. Engl. 1988, 27, 304-306.
43. [18a] R. Boese, D. Bläser, Angew. Chem. 1988, 100, 293-295; Angew. Chem. Int. Ed. Engl. 1988, 27, 304-306.
44. [18b] F. Toda, K. Tanaka, Z. Stein, I. Goldberg, Acta Crystallogr. Sec. C 1996, 52, 177-180.
45. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 109-220.
46. [20a] E. F. Ullman, K. R. Huffman, Tetrahedron Lett. 1965, 23, 1863-1867.
47. [20b] R. M. Wilson, K. Hannemann, K. Peters, E.-M. Peters, J. Am. Chem. Soc. 1987, 109, 4741-4743.
48. WINSIM, Author: D. R. Duling, Laboratory of Molecular Biophysics, NIEHS, NIH, Research Triangle Park, North Carolina; see: D. R. Duling, J. Magn. Reson. B. 1994, 104, 105-110.
49. WINSIM, Author: D. R. Duling, Laboratory of Molecular Biophysics, NIEHS, NIH, Research Triangle Park, North Carolina; see: D. R. Duling, J. Magn. Reson. B. 1994, 104, 105-110.
50. H. Kurrek, B. Kirste, W. Lubitz, Electron Nuclear Double Resonance Spectroscopy of Radicals in Solution, VCH, Weinheim, 1988.