Rearrangement of indene skeletons under mild conditions

Journal of Organic Chemistry

Volumn 72, Issue 18, 2007, Pages 6749-6752

  Kuninobu, Yoichiro ^a   Ueda, Hirokazu ^a   Kawata, Atsushi ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HIGH TEMPERATURE EFFECTS; IRRADIATION; ISOMERIZATION; ISOMERS; ULTRAVIOLET RADIATION;

INDENE DERIVATIVES; INDENE SKELETONS; UV LIGHT IRRADIATION;

HYDROCARBONS;

INDENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HIGH TEMPERATURE; IRRADIATION; ISOMER; ISOMERIZATION; REACTION ANALYSIS; ROOM TEMPERATURE; ULTRAVIOLET IRRADIATION;

EID: 34548715205     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070537w     Document Type: Article

References (53)

1. (a) Fitty, R. Ann. 1860, 114, 54.
2. (b) Blicke, F.; Azuara, J.; Doorenbos, N.; Hotelling, E. J. Am. Chem. Soc. 1953, 75, 5418.
3. (c) Mundy, B. P.; Srinivasa, R.; Otzenberger, R. D.; Debernardis, A. R. Tetrahedron Lett. 1979, 2673.
4. (d) Olah, J. A. J. Org. Chem. 1997, 62, 6666.
5. (e) Shinohara, T.; Suzuki, K. Tetrahedron Lett. 2002, 43, 6937.
6. (a) Wagner, G. J. Russ. Phys. Chem. Soc. 1899, 31, 690.
7. (b) Meerwein, H. Ann. 1914, 405, 129.
8. (c) Sorensen, T. S. Acc. Chem. Res. 1976, 9, 257.
9. (d) Fitjer, L.; Wehle, D.; Noltemeyer, M.; Egert, E.; Sheldrick, G. M. Chem. Ber. 1984, 117, 203.
10. (e) Paquette, L. A.; Waykole, L.; Jendralla, H.; Cottrell, C. E. J. Am. Chem. Soc. 1986, 108, 3739.
11. (a) Beckmann, E. Ber. 1886, 19, 988.
12. (b) Beckmann, E. Ber. 1887, 20, 1507.
13. (c) Ruzicka, L.; Kobelt, M.; Hafliger, O.; Prelog, V. Helv. Chim. Acta. 1949, 32, 544.
14. (d) Meth-Cohn, O.; Narine, B. Synthesis 1980, 133.
15. (e) Sharghi, H.; Hosseini, M. Synthesis 2002, 1057.
16. (f) Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667.
17. (a) Cope, A. C.; Hardy, E. M. J. Am. Chem. Soc. 1940, 62, 441.
18. (b) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1.
19. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205.
20. (d) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 388.
21. (e) Nubbemeyer, U. Synthesis 2003, 961.
22. (a) Neureiter, N. P. J. Org. Chem. 1959, 24, 2044.
23. (b) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. Org. React. 1985, 33, 247.
24. (c) Zimmerman, H. E.; Fleming, S. A. J. Am. Chem. Soc. 1983, 105, 622.
25. (d) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939.
26. (a) Zimmerman, H. E.; Grunewald, G. L. J. Am. Chem. Soc. 1966, 88, 183.
27. (b) Zimmerman, H. E. Angew. Chem., Int. Ed. Engl. 1969, 8, 1.
28. (c) Hixson, S. S.; Mariano, P. S.; Zimmerman, H. E. Chem. Rev. 1973, 73, 531.
29. (d) Paquette, L. A.; Bay, E.; Yeh, Ku, A.; Rondan, N. G.; Houk, K. N. J. Org. Chem. 1982, 47, 422.
30. (e) Demuth, M.; Mikhail, G. Synthesis 1989, 145.
31. (f) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065.
32. (a) Zimmerman, H. E.; Hovey, M. C. J. Org. Chem. 1979, 44, 2331.
33. (b) Zimmerman, H. E.; Kreil, D. J. J. Org. Chem. 1982, 47, 2060.
34. (c) Hughes, R. P.; Trujillo, H. A.; Egan, J. W., Jr.; Rheingold, A. L. J. Am. Chem. Soc. 2000, 122, 2261.
35. (a) Koelsch, C. F.; Johnson, P. R. J. Am. Chem. Soc. 1943, 65, 567.
36. (b) Miller, L. L.; Boyer, R. F. J. Am. Chem. Soc. 1971, 93, 650.
37. (a) Padwa, A.; Loza, R.; Getman, D. Tetrahedron Lett. 1977, 33, 2847.
38. (b) Palensky, F. J.; Morrison, H. A. J. Am. Chem. Soc. 1977, 99, 3507.
39. (c) Padwa, A.; Blacklock, T. J.; Getman, D.; Hatanaka, N.; Loza, R. J. Org. Chem. 1978, 43, 1481.
40. (d) Giacherio, D.; Morrison, H. J. Am. Chem. Soc. 1978, 100, 7109.
41. (e) Padwa, A.; Goldstein, S.; Loza, R.; Pulwer, M. Tetrahedron Lett. 1979, 51, 4895.
42. (f) Morrison, H.; Giacherio, D.; Balensky, F. J. J. Org. Chem. 1982, 47, 1051.
43. (g) Duguid, R. J.; Morrison, H. J. Am. Chem. Soc. 1991, 113, 3519.
44. (a) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498.
45. (b) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.
46. 2, the rate of isomerization was increased and indene isomer 4a was obtained in 92% yield.
47. The isomerization rates of 3a to 4a in N,N-dimethylformamide at 100°C for 3 h were changed when the reactions were carried out under different concentrations (4a: 43% (0.40 M); 38% (0.20 M); 27% (0.10 M); 18% (0.050 M).). One possible explanation of this result is that 4a was formed via intramolecular isomerization, which was influenced by the amino group of another molecule. In fact, by adding a base (1.0 equiv) in the reaction mixture, the accelerating effect of the base was observed (0.20 M, none: 38%; aniline: 61%; piperidine: >99%).
48. 80°C (4a: 90%; 3a: 10%); 50°C (4a: 17%; 3a: 82%).
49. For the theoretical calculations of the isomerization of indene derivatives via radical intermediates, see: Dubnikova, F.; Lifshitz, A. Isr. J. Chem. 2003, 43, 325.
50. Fieser, M.; Fieser, L. F. Org. Synth. 1972, 3, 26.
51. Hunsen, M. Tetrahedron Lett. 2005, 46, 1651.
52. Negishi, E.-i.; King, A. O.; Klima, W. L. J. Org. Chem. 1980, 45, 2526.
53. Crandall, J. K.; Michaely, W. J. J. Org. Chem. 1984, 49, 4244.