Approaches to open fullerenes: Synthesis and thermal stability of cis-1 bis(isobenzofuran) Diels-Alder adducts of C60

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 2724-2731

  Sander, Michael ^a   Jarrosson, Thibaut ^a   Chuang, Shih Ching ^a   Khan, Saeed I ^a   Rubin, Yves ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SATURATION (MATERIALS COMPOSITION); SOLUBILITY; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS;

ALDER ADDUCTS; ISOBENZOFURANS; SOLUBILIZATION; X-RAY STRUCTURE;

FULLERENES;

FULLERENE DERIVATIVE; ISOBENZOFURAN DERIVATIVE; QUINOXALINE DERIVATIVE; TETRAZINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMOGRAVIMETRY; THERMOSTABILITY; X RAY ANALYSIS;

BENZOFURANS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FULLERENES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; TEMPERATURE;

EID: 34247193693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061987b     Document Type: Article

References (47)

1. See the preceding article in this issue: Chuang, S.-C.; Jarrosson, T.; Sander, M.; James, S.; Rozumov, E.; Khan, S. I.; Rubin, Y. J. Org. Chem. 2007, 72, 2716-2723.
2. (a) Arce, M. J.; Viado, A. L.; An, Y. Z.; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 1996, 118, 3775-3776.
3. Chuang, S.-C.; Clemente, F. R.; Khan, S. I.; Houk, K. N.; Rubin, Y. Org. Lett. 2006, 8, 4525-4528.
4. (a) Diederich, F.; Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263-277.
5. (b) Diederich, F.; Kessinger, R. Acc. Chem. Res. 1999, 32, 537-545.
6. (c) Qian, W.; Rubin, Y. Angew. Chem., Int. Ed. 2000, 39, 3133-3137.
7. (d) Qian, W.; Rubin, Y. J. Am. Chem. Soc. 2000, 122, 9564-9565.
8. (e) Qian, W.; Rubin, Y. Angew. Chem., Int. Ed. 1999, 38, 2356-2360.
9. Herzog, A.; Hirsch, A.; Vostrowsky, O. Eur. J. Org. Chem. 2000, 171-180.
10. (f) Djojo, F.; Hirsch, A.; Grimme, S. Eur. J. Org. Chem. 1999, 3027-3039.
11. (g) Echegoyen, L. E.; Djojo, F. D.; Hirsch, A.; Echegoyen, L. J. Org. Chem. 2000, 65, 4994-5000.
12. (h) Reuther, U.; Brandmüller, T.; Donaubauer, W.; Hampel, F.; Hirsch, A. Chem. Eur. J. 2002, 8, 2261-2273.
13. (l) Thilgen, C.; Diederich, F. C. R. Acad. Sci., Ser. IIc: Chim. 2006, 9, 868-880.
14. (a) Bourgeois, J.-P.; Echegoyen, L.; Fibbioli, M.; Pretsch, E.; Diederich, F. Angew. Chem., Int. Ed. 1998, 37, 2118-2121.
15. (b) Qian, W.; Rubin, Y. J. Am. Chem. Soc. 2000, 122, 9564-9565.
16. (c) Qian, W.; Rubin, Y. Angew. Chem., Int. Ed. 1999, 38, 2356-2360.
17. (d) Qian, W.; Rubin, Y. Angew. Chem., Int. Ed. 2000, 39, 3133-3137.
18. (e) Qian, W.; Rubin, Y. J. Org. Chem. 2002, 67, 7683-7687.
19. (a) Hirsch, A.; Lampanti, I.; Karfunkel, H. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 437-438.
20. (b) Reuther, U.; Brandmüller, T.; Donaubauer, W.; Hampel, F.; Hirsch, A. Chem. Eur. J. 2002, 8, 2261-2273.
21. (a) Jensen, A. W.; Khong, A.; Saunders, M.; Wilson, S. R.; Schuster, D. I. J. Am. Chem. Soc. 1997, 119, 7303-7307.
22. (b) Kanakamma, P. P.; Huang, S. L.; Juo, C. G.; Her, G. R.; Luh, T. Y. Chem. Eur. J. 1998, 4, 2037-2042.
23. (c) Hsiao, T. Y.; Chidambareswaran, S. K.; Cheng, C. H. J. Org. Chem. 1998, 63, 6119-6122.
24. (d) Rubin, Y.; Ganapathi, P. S.; Franz, A.; An, Y.-Z.; Qian, W.; Neier, R. Chem. Eur. J. 1999, 5, 3162-3184.
25. Stiles, M.; Miller, R. G. J. Am. Chem. Soc. 1960, 82, 3802.
26. See Experimental Section.
27. (a) Sauer, J. In Comprehensive Heterocyclic Chemistry 2; Pergamon Press: Oxford, 1996; Vol. 6, pp 901-957.
28. (b) Sauer, J.; Heldmann, D. K.; Hetzenegger, J.; Krauthan, J.; Sichert, H.; Schuster, J. Eur. J. Org. Chem. 1998, 2885-2896.
29. (a) Murata, Y.; Suzuki, M.; Rubin, Y.; Komatsu, K. Bull. Chem. Soc. Jpn. 2003, 76, 1669-1672.
30. (b) Miller, G. P.; Tetreau, M. C.; Olmstead, M. M.; Lord, P. A.; Balch, A. L. Chem. Commun. 2001, 1758-1759.
31. (a) Stetter, H.; Ramsch, R. Y.; Kuhlmann, H. Synthesis 1976, 733-736.
32. (b) Firouzabadi, H.; Karimi, B.; Abbassi, M. Chem. Res., Synop. 1999, 3, 236-237.
33. (c) Abdel-Jalil, J.; Al-Qawasmeh, R. A.; Voelten W.; Heeg, P.; El-Abadelah, M. M.; Sabri, S. S. J. Heterocycl. Chem. 2000, 37, 1273-1275.
34. Vilsmeier, A.; Haack, A. Ber. 1927, 60, 119.
35. (a) Warrener, R. N. J. Am. Chem. Soc. 1971, 93, 2346-2348.
36. (b) Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135-241.
37. (c) Rodrigo, R. Tetrahedron 1988, 44, 2093-2135.
38. (d) Rickborn, B. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1, pp 1-134.
39. (e) Bird, C. W. Prog. Heterocycl. Chem. 1990, 2, 87-101.
40. (f) Peters, O.; Friedrichsen, W. Trends Heterocycl. Chem. 1995, 4, 217-259.
41. (a) Fullerenes and Related Structures; Hirsch, A., Ed.; Topics in Current Chemistry 199; Springer: Berlin, New York, 1999.
42. (b) Rubin, Y.; Diederich, F. In Stimulating Concepts in Chemistry; Wiley-VCH: New York, 2000; pp 163-186.
43. (c) Kordatos, K.; Da Ros, T.; Prato, M.; Bensasson, R. V.; Leach, S. Chem. Phys. 2003, 293, 263-280.
44. (a) Kordato, K.; Bosi, S.; Da Ros, T.; Zambon, A.; Lucchini, V.; Prato, M. J. Org. Chem. 2001, 66, 2802-2808.
45. (b) Nakamura, Y.; Takano, N.; Nishimura, T.; Yashima, E.; Sato, M.; Kudo, T.; Nishimura, J. Org. Lett. 2001, 3, 1193-1196.
46. (a) Chute, W. J.; Orchard, W. M.; Wright, G. F. J. Org. Chem. 1941, 6, 157-168.
47. (b) Nazarova, Z. N.; Potemkin, G. F. Zh. Obshchei Khim. 1965, 1, 1709-1710.