Radical-radical interaction through a saturated link: Methylenebis-6- oxoverdazyl

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4889-4895

  Brook, David J R ^a   Yee, Gordon T ^b  

^a SANTA CLARA UNIVERSITY   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GROUND STATE; ORGANOMETALLICS; REACTION KINETICS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

NONCONJUGATED RADICAL CENTERS; RADICAL-RADICAL INTERACTION; SATURATED LINKS; UV-VIS SPECTRUM;

FREE RADICALS;

ALKANE; BENZOQUINONE; BIS(TETRAZANE); METHYLENEBIS(1,5 DIISOPROPYL 6 OXOVERDAZYL); METHYLENEBISOXOVERDAZYL; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; ELECTRON; EXCITED STATE; GROUND STATE; MAGNETISM; MOLECULAR INTERACTION; OXIDATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 33745461231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060165b     Document Type: Article

References (44)

1. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995.
2. Borden, W. T. Diradicals; Wiley: New York, 1982.
3. Lahti, P. M. Molecular Magnetism in Organic-Based Materials; Marcel Dekker: New York, 1999.
4. Kahn, O. Molecular Magnetism; VCH: New York, 1993.
5. Bonacic-Koutecky, V.; Koutecky, J.; Michl, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 170-189.
6. Salem, L.; Rowland, C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92-111.
7. Rajca, A.; Rajca, S. J. Am. Chem. Soc. 1996, 118, 8121-8126.
8. Rajca, A.; Shiraishi, K.; Vale, M.; Han, H.; Rajca, S. J. Am. Chem. Soc. 2005, 127, 9014-9020.
9. Luckhurst, G. R.; Pedulli, G. F.; Tiecco, M. J. Chem. Soc. B 1971, 329.
10. Fang, S.; Lee, M. S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1995, 117, 6727-6731.
11. Fujita, J.; Tanaka, M.; Suemune, H.; Koga, N.; Matsuda, K.; Iwamura, H. J. Am. Chem. Soc. 1996, 118, 9347-9351.
12. Oshio, H.; Makato, U.; Fukushi, T.; Ito, T. Chem. Lett. 1997, 1065-1066.
13. Calder, A.; Forrester, A. R.; James, P. G.; Luckhurst, G. R. J. Am. Chem. Soc. 1969, 91, 3724-3727.
14. Kawakami, T.; Yamanaka, S.; Mori, W.; Yamaguchi, K.; Kajiwara, A.; Kamachi, M. Chem. Phys. Lett. 1995, 235, 414-421.
15. Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 847-850.
16. Wautelet, P.; Le Moigne, J.; Videva, V.; Turek, P. J. Org. Chem. 2003, 68, 8025-8036.
17. Stroh, C.; Zeissel, R.; Raudaschl-Sieber, G.; Kohler, F. H.; Turek, P. J. Mater. Chem. 2005, 15, 850-858.
18. Cansechi, A.; Dei, A.; Lee, H.; Shultz, D. A.; Sorace, L. Inorg. Chem. 2001, 40, 408-411.
19. Shultz, D. A.; Bodnar, S. H.; Lee, H.; Kampf, J. W.; Incarvito, C. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 10054-10061.
20. Shultz, D. A.; Bodnar, S. H.; Kumar, R. K.; Lee, H.; Kampf, J. W. Inorg. Chem. 2001, 40, 546-549.
21. Shultz, D. A.; Boal, A. K.; Farmer, G. T. J. Am. Chem. Soc. 1997, 119, 3846-3847.
22. Fico Jr., R. M.; Hay, M. F.; Reese, S.; Hammond, S.; Lambert, E.; Fox, M. A. J. Org. Chem. 1999, 64, 9386-9392.
23. Horsley, J. A.; Jean, Y.; Moser, C.; Salem, L.; Stevens, R. M.; Wright, J. S. J. Am. Chem. Soc. 1972, 94, 279-282.
24. Goldberg, A. H.; Dougherty, D. A. J. Am. Chem. Soc. 1983, 105, 284-290.
25. Doubleday, C., Jr.; McIver, J. W., Jr.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533-6542.
26. Hoffman, R. Acc. Chem. Res. 1971, 4, 1-9.
27. Buchwalter, S. L.; Closs, G. L. J. Am. Chem. Soc. 1979, 101, 4688-4694.
28. Abe, M.; Adam, W.; Borden, W. T.; Hattori, M.; Hrovat, D. A.; Nojima, M.; Nozaki, K.; Wirz, J. J. Am. Chem. Soc. 2004, 126, 574-582.
29. Okumura, M.; Takada, K.; Maki, J.; Noro, T.; Mori, W.; Yamaguchi, K. Mol. Cryst. Liq. Cryst. 1993, 41-60.
30. Keana, J. F. W.; Norton, R. S.; Morello, M.; Van Engen, D.; Clardy, J. J. Am. Chem. Soc. 1978, 100, 934-937.
31. Franzen, S.; Shultz, D. A. J. Phys. Chem. A 2003, 107, 4292-4299.
32. Shultz, D. A. J. Am. Chem. Soc. 2001, 123, 6431-6432.
33. Frank, N. L.; Clerac, R.; Sutter, J.-P.; Daro, N.; Kahn, O.; Coulon, C.; Green, M. T.; Golhen, S.; Ouahab, L. J. Am. Chem. Soc. 2000, 122, 2053-2061.
34. Paré, E. C.; Brook, D. J. R.; Brieger, A.; Badik, M.; Schinke, M. Org. Biomol. Chem. 2005, 3, 4258-4261.
35. Brook, D. J. R.; Fox, H. H.; Lynch, V.; Fox, M. A. J. Phys. Chem. 1996, 100, 2066.
36. Duling, D. R. J. Magn. Res. Ser. B 1994, 104, 105-110.
37. Prasad, B. L. V.; Radhakrishnan, T. P. THEOCHEM 1996, 361, 175-180.
38. Bleaney, B.; Bowers, K. D. Proc. R. Soc. London 1952, A214, 451.
39. Neugebauer, F. A.; Fischer, H.; Siegel, R. Chem. Ber. 1988, 121, 815.
40. Barr, C. L.; Chase, P. A.; Hicks, R. G.; Lemaire, M. T.; Stevens, C. L. J. Org. Chem. 1999, 64, 8893.
41. Neugebauer, F. A.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1980, 92, 761.
42. Barone, V.; Bencini, A.; Ciofini, I.; Daul, C. J. Phys. Chem. A 1999, 103, 4275-4282.
43. Green, M. T.; McCormick, T. A. Inorg. Chem. 1999, 38, 3061-3065.
44. Chung, G.; Lee, D. Chem. Phys. Lett. 2001, 350, 339-344.