Electrochemical, ESR and quantum chemical study of 1-substituted naphthalenes and their radical anions

Journal of Physical Organic Chemistry

Volumn 21, Issue 1, 2008, Pages 73-78

  Vasilieva, N V ^a   Irtegova, I G ^a   Vaganova, T A ^a   Shteingarts, V D ^a,b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

Cyclic voltammetry; Electrochemical oxidation; Electrochemical reduction; ESR spectroscopy; Naphthalene derivatives; Radical anions; Radical cations

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROCHEMICAL OXIDATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; NAPHTHALENE; SUBSTITUTION REACTIONS;

ELECTROCHEMICAL REDUCTION; NAPHTHALENE DERIVATIVES; RADICAL ANIONS; RADICAL CATIONS;

QUANTUM CHEMISTRY;

EID: 39349092362     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1288     Document Type: Article

References (43)

1. E. V. Panteleeva, M. Yu. Lukyanova, L. M. Pokrovsky, V. D. Shteingarts, Russ. Chem. Bull. 2007, N6, 1069-1077.
2. a) 1.1. Bilkis, V. D. Shteingarts, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., Int. Ed. Engl. 1987, 17, 105;
3. b) T. A. Vaganova, E. V. Panteleeva, V. D. Shteingarts, Reductive Alkylation of Arenecarbonitriles: Synthetic Aspects, in The Panorama of Modern Chemistry in Russia. Modern Organic Synthesis, Khimiya, Moscow, 2003, 293 (in Russian).
4. a) C. K. Mann, K. K. Barnes, Electrochemical Reactions In Nonaqueous Systems, Marcel Dekker, New York, 1970. (rus-479 p);
5. b) Encyclopedia of Electrochemistry of the Elements. Organic Section, vol. XI-XV. (Eds: A. J. Bard, H. Lund,) Marcel Dekker, New Jork, Basel.
6. a) W. Kemula, R. Sioda, J. Electroanal. Chem. 1964, 7, 233-241;
7. b) A. S. Mendkovich, A. P. Churilina, L. V. Mikhal'chenko, V. P. Gul'tyai, Bull. Acad. Sci. USSR, Div. Chem. Sci., Int. Ed. Engl. 1990, 39, 1348-1351;
8. c) H. Bock, U. Lechner-Knoblauch, Z. Naturforsch. B 1985, 40, 1463-1475;
9. d) G. Anthoine, J. Nascelski, B. Wilmet-Devos, Bull. Soc. Chim. Belg. 1969, 78, 465-469;
10. e) A. Hatano, R. Hatano, Yakugaku Zasshi 1973, 93, 910-915 (Chem. Abstr. 79, 77730);
11. f) A. S. Mendkovich, A. P. Churilina, L. V. Mikhal'chenko, V. P. Gul'tyai, Bull. Acad. Sci. USSR, Div. Chem. Sci., Int. Ed. Engl. 1991, 40, 1572-1577;
12. g) L. Ya. Kheifets, V. D. Bezuglyi, J. Gen. Chem. USSR, Int. Ed. Engl. 1971, 47, 507-511;
13. h) N. M. Przhiyalgovskaya, L. Ya. Kheifets, L. I. Dmitrievskaya, V. D. Bezuglyi, J. Gen. Chem. USSR, Int. Ed. Engl. 1971, 47, 1114-1117;
14. j) V. V. Yanilkin, N. I. Maksimyuk, E. I. Gritsenko, Yu. M. Kargin, Bull. Russ. Acad. Sci., Div. Chem. Sci., Int. Ed. Engl. 1992, 41, 1363-1367;
15. k) Yu. M. Kargin, Yu. G. Budnikova, V. V. Yanilkin, J. Gen. Chem. USSR, Int. Ed. Engl. 1991, 61, 1816-1820;
16. l) A. Streitwieser, J. Schwager, J. Phys. Chem. 1962, 66, 2316-2320;
17. m) V. S. Dunyashev, E. A. Polenov, N. E. Minina, V. M. Kazakova, G. A. Grigor'ev, L. M. Yagupol'skii, J. Gen. Chem. USSR, Int. Ed. Engl. 1988, 58, 178-181;
18. n) E. Brillas, J. M. Costa, An. Quim. Ser. A 1980, 76, 321-324;
19. o) C. Koper, L. W. Jenneskens, M. Sarobe, Tetrahedron Lett. 2002, 43, 3833-3836;
20. p) P. Given, M. Peover, J. Chem. Soc. 1960, 385-387;
21. q) T. M. Krygowsky, M. Stencel, Z. Galus, J. Electroanal. Chem. 1972, 39, 395-405;
22. r) C. Lagrost, D. Carrie, M. Vaultier, P. Hapiot, J. Phys. Chem. A 2003, 107, 745-752;
23. s) M. A. Fox, C. C. Chen, J. N. N. Younathan, J. Org. Chem. 1984, 49, 1969-1974.
24. a) E. S. Pysh, N. C. Yang, J. Am. Chem. Soc. 1963, 85, 2124-2130;
25. b) A. Zweig, R. H. Mauer, B. G. Roberts, J. Org. Chem. 1967, 32, 1322-1329;
26. c) C. Parkanyi, P. Zahradnik, Collect. Czech. Chem. Commun. 1965, 30, 4287-4296;
27. d) M. Sakamoto, X. Cai, M. Hara, M. Fujitsuka, T. Majima, J. Am. Chem. Soc. 2004, 126, 9709-9714;
28. e) P. H. Milne, D. D. M. Wayner, D. P. DeCosta, J. A. Pincock, Can. J. Chem. 1992, 70, 121-127.
29. N. V. Vasil'eva, V. F. Starichenko, V. A. Koptyug, J. Org. Chem. USSR, Int. Ed. Engl. 1987, 23, 921-929.
30. K. Möbius, Z. Naturforsch. A 1965, 20, 1093-1117.
31. a) K. K. Sharma, R. J. Boyd, J. Chem. Soc., Faraday Trans. II 1979, 75, 494-499;
32. b) S. Brumby, J. Magn. Reson. 1980, 40, 157-165.
33. P. Furderer, F. Gerson, Helv. Chim. Acta 1976, 59, 2492-2498.
34. D. N. Laikov, Chem. Phys. Lett. 1997, 281, 151-156.
35. N. Donaldson, The Chemistry and Technology of Naphthalene Compounds, E. Arnold & Co., London, 1958. 512 p.
36. F. F. Blicke, J. Am. Chem. Soc. 1927, 49, 2843-2849.
37. G. M. Coppinger, J. Am. Chem. Soc. 1954, 76, 1372-1373.
38. H. C. Brown, A. Tsukamoto, J. Am. Chem. Soc. 1964, 86, 1089-1095.
39. P. J. Card, F. E. Friedli, H. Shechter, J. Am. Chem. Soc. 1983, 105, 6104-6114.
40. F. F. Blicke, C. E. Maxwell, J. Am. Chem. Soc. 1939, 61, 1780-1783.
41. N. V. Vasil'eva, V. F. Starichenko, L. N. Shchegoleva, Zh. Org. Khim. 1998, 34, 1650-1659.
42. R. Improta, V. Barone, Chem. Rev. 2004, 104, 1231-1253.
43. I. I. Bilkis, T. A. Vaganova, A. J. Denisov, V. D. Shteingarts, Zh. Org. Khim. 1987, 23, 2062-2070.