Reactivity of triarylphosphine peroxyl radical cations generated through the reaction of triarylphosphine radical cations with oxygen

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8227-8232

  Tojo, Sachiko ^a   Yasui, Shinro ^b   Fujitsuka, Mamoru ^a   Majima, Tetsuro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b TEZUKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON OXIDATION; ELECTRON-RELEASING SUBSTITUENTS; TRIARYLPHOSPHINE PEROXYL;

ABSORPTION; AROMATIC COMPOUNDS; ELECTRONS; OXIDATION; REACTION KINETICS; SUBSTITUTION REACTIONS;

POSITIVE IONS;

BENZONITRILE; CATION; METHYL GROUP; OXYGEN; PEROXY RADICAL; PHENYL GROUP; PHOSPHINE DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ABSORPTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; OXIDATION; REACTION ANALYSIS;

EID: 33750019971     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061319q     Document Type: Article

References (41)

1. (a) Powell, R. L.; Hall, C. D. J. Am. Chem. Soc. 1969, 91, 5403.
2. (b) Pandey, G.; Hajra, S.; Chorai, M. K.; Kumar, K. R. J. Am. Chem. Soc. 1997, 119, 8777.
3. (c) Pandey, G.; Pooranchand, D.; Bhalerao, U. T. Tetrahedron Lett. 1991, 47, 1745.
4. (d) Yasui, S.; Shioji, K.; Ohno, A.; Yoshihara, M. J. Org. Chem. 1995, 60, 2099.
5. (e) Shukla, D.; Lu, C.; Schepp, N. P.; Bentrude, W. G.; Johnston, L. J. J. Org. Chem. 2000, 65, 6167.
6. (f) Yasui, S.; Shioji, K.; Tsujimoto, M.; Ohno, A. J. Chem. Soc., Perkin Trans. 2 1999, 855-862.
7. (a) Zagumennov, V. A.; Nikitin, E. V. Russian. J. Electrochem. 2003, 39, 1380.
8. (b) Yasui, S.; Shioji, K.; Tsujimoto, M.; Ohno, A. Heteroatom Chem. 2000, 11, 152.
9. Nakamura, M.; Miki, M.; Majima, T. J. Chem. Soc., Perkin Trans. 2 2000, 1447.
10. (a) Alfassi, Z. B.; Neta, P.; Beaver, B. J. Phys. Chem. A 1997, 101, 2153.
11. (b) Beaver, B.; Rawlings, D.; Neta, P.; Alfassi, Z. B.; Das, T. N. Heteroatom Chem. 1998, 9, 133.
12. (a) Yasui, S.; Tojo, S.; Majima, T. J. Org. Chem. 2005, 70, 1276.
13. (b) Yasui, S.; Tojo, S.; Majima, T. Org. Biomol. Chem. 2006, 4, 2969.
14. Kira, A.; Thomas, J. K. J. Phys. Chem. 1974. 78, 2094.
15. (b) Kira, A.; Imamura, M. J. Phys. Chem. 1979, 83, 2267.
16. Burrows, H. D.; Greatorex, D.; Kemp, T. J. J. Phys. Chem. 1972, 76, 20.
17. Gara, W. B.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1978, 150.
18. Fukuzumi, S.; Imahori, H.; Yamada, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Guldi, D. M. J. Am. Chem. Soc. 2001, 123, 2571.
19. Dincturk, S.; Jackson, R. A.; Townson, M.; Agirbas, H. B.; Billingham, N. C.; Mach, G. J. Chem. Soc., Perkin Trans. 2 1981, 1121.
20. (a) Sakaguchi, Y.; Hayashi, H. Chem. Phys. Lett. 1995, 245, 591.
21. (b) Sakaguchi, Y.; Hayashi, H. J. Phys. Chem. A 2004, 108, 3421.
22. (a) Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095.
23. (b) Tokumura, K.; Ozaki, T.; Nosaka, H.; Saigusa, E. Y.; Itoh, M. J. Am. Chem. Soc. 1991, 113, 4974.
24. Nelsen, S. F. Acc. Chem. Res. 1987, 20, 269.
25. (a) Tojo, S.; Morishima, K.; Ishida, A.; Majima, T.; Takamuku, S. J. Org. Chem. 1995, 60, 4684.
26. (b) Majima, T.; Tojo, S.; Ishida, A.; Takamuku, S. J. Org. Chem. 1996, 61, 7793.
27. (c) Majima, T.; Tojo, S.; Ishida, A.; Takamuku, S. J. Phys. Chem. 1996, 100, 13615.
28. (d) Hara, M.; Samori, S.; Xichen, C.; Fujitsuka, M.; Majima, T. J. Org. Chem. 2005, 70, 4370.
29. Mizuno, K.; Tamai, T.; Hashida, I.; Otsuji, Y.; Kuriyama, Y.; Tokumaru, K. J. Org. Chem. 1994, 59, 7329.
30. Fujita, M.; Shindo, A.; Ishida, A.; Majima, T.; Takamuku, S.; Fukuzumi, S. Bull. Chem. Soc. Jpn. 1996, 69, 743.
31. Suga, K.; Okubo, K.; Fukuzumi, S. J. Phys. Chem. A 2003, 107, 4339.
32. Tsuchiya, M.; Ebbesen, T. W.; Nishimura, Y.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1987, 2121.
33. Berclaz, T.; Geoffroy, M. Mol. Phys. 1975, 30, 549.
34. Culcasi, M.; Berchadsky, Y.; Grounchi, G.; Tordo, P. J. Org. Chem. 1991, 56, 3537.
35. (a) Alfassi, Z. B.; Mosseri, S.; Neta, P. J. Phys. Chem. 1987, 91, 3383.
36. (b) Schoneich, C.; Aced, A.; Asmus, K. D. J. Am. Chem. Soc. 1991, 113, 375.
37. (a) Furimsky, E.; Howard, J. A.; J. Am. Chem. Soc. 1973, 95, 369.
38. (b) Bentrude, W. G. Acc. Chem. Res. 1982, 15, 117.
39. Sonntag, C.; Schuchmann, H. P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229.
40. Flyunta, R.; Makogonb, O.; Asmus, K. D. Radiat. Phys. Chem. 2002, 65, 299.
41. Fukuzumi, S.; Shimoosako, K.; Suenobu, T.; Watanabe, Y. J. Am. Chem. Soc. 2003, 125, 9074.