Cyclopropyl- and allyl-substituted arenes in reaction with dinitrogen tetroxide. Effect of substrate oxidation potential on reaction direction

Russian Journal of Organic Chemistry

Volumn 40, Issue 8, 2004, Pages 1098-1112

  Mochalov, S S ^a   Gazzaeva, R A ^b   Fedotov, A N ^a   Trofimova, E V ^a   Trushkov, I V ^a   Zefirov, N S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b NORTH OSSETIAN STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NITRO COMPOUND; CYCLOPROPANE DERIVATIVE; NITROGEN DIOXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CORRELATION ANALYSIS; ELECTRON TRANSPORT; EMPIRICISM; ENERGY; OXIDATION KINETICS; OXIDATION REDUCTION POTENTIAL; RING OPENING;

EID: 7244239407     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUJO.0000045888.43245.d7     Document Type: Article

References (25)

1. Smirnova, M.M., Geiderikh, A.V., Mochalov, S.S., and Shabarov, Yu. S., Zh. Org. Khim., 1988, vol. 24, p. 1189.
2. Mochalov, S.S., Kuz'min, Ya.I., Fedotov, A.N., Trofimova, E.V., Gazzaeva, R.A., Shabarov, Yu.S., and Zefirov, N.S., Zh. Org. Khim., 1998, vol. 34, p. 1379.
3. Mochalov, S.S., Gazzaeva, R.A., Atanov, V.N., Fedotov, A.N., and Zefirov, N.S., Khim. Geterotsikl. Soed., 1999, p. 324.
4. Rosokha, S.V. and Kochi, J.K., J. Am. Chem. Soc., 2001, vol. 123, p. 8985.
5. Gaussian, 98, Revision, A.7; Frisch, M.J., Trucks, G.W., Schiegei, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Jr., Stratmann, R.E., Burant, J.C., Dapprich, S., Millan, J.M., Daniels, A.D., Kudin, K.N. Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Cllifford, S., Ochterski, J., Petersson, G.A., Ayaia, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortis, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., AI-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Repiogie, E.S., and Pople, J.A., Gaussian, Inc., Pittsburgh, PA, 1998.
6. Dewar, M.J.S., Zoebisch, E.G., and Healy, E.F., J. Am. Chem. Soc., 1985, vol. 107, p. 3902.
7. Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, p. 724.
8. Petersson, G.A., Bennett, A., Tensfeldt, T.G., Al-Laham, M.A., Shirley, W.A., and Mantzaris, J., J. Chem. Phys., 1988, vol. 89, p. 2193.
9. Somich, C., Mazzocchi, P., Edwards, M., Morgan, T., and Ammon, H.L., J. Org. Chem., 1990, vol. 55, p. 2624.
10. Takahashi, Y., Ohaku, H., Nishioka, N., Ikeda, H., Miyashi, T., Gormin, D.A., and Hilinski, E.F., J. Chem. Soc., Perkin, Trans. II, 1997, p. 303.
11. Prins, I., Verhoeven, J.W., de, Boer, Th.J., and Worrell, C., Tetrahedron, 1977, vol. 33, p. 127.
12. Shudo, K., Kobayashi, T., and Utsunomiya, C., Tetrahedron, 1977, vol. 33, p. 1721.
13. Clark, T., A Handbook of Computational Chemistry, New York:Wiley, 1985.
14. Samodov, A.A., Mochalov, S.S., and Shchapin, I.Yu., Abstract of Papers, Int. Conf. "Reaction Mechanisms and Organic Intermediates", St. Petersburg, Russia, 2001, p. 137.
15. Roth, H.D., Herbertz, T., Lakkaraju, P.S., Sluggett, G., and Turro, N.J., J. Phys. Chem. A, 1999, vol. 103, p. 11350.
16. Mochalov, S.S., Karpova, V.V., and Shabarov, Yu.S., Zh. Org. Khim., 1980, vol. 16, p. 1413.
17. Fedotov, A.N., Trofimova, E.V., Mochalov, S.S., and Shabarov, Yu.S., Zh. Org. Khim., 1988, vol. 24, p. 1413.
18. Beizeeki, C., Bull. Acad. Pol. Sci., Ser. Sci. Chem., 1963, vol. 11, p. 21.
19. Grinwold, A.A. and Stracher, P.S., J. Org. Chem., 1966, vol. 31, p. 121.
20. Shoenbrunn, E.F. and Gardner, Y.H., J. Am. Chem. Soc., 1960, vol. 82, p. 4905.
21. Brand, Y. and Stevens, I., J. Chem. Soc., 1958, p. 629.
22. Mochalov, S.S., Atanov, V.A., and Zefirov, N.S., Khim. Geterotsikl. Soed., 1998, p. 618.
23. Levina, R.Ya., Shabarov, Yu.S., Shanazarov, K.S., and Treshchova, E.G., Vestn. MGU, Ser. 2, Khim., 1957, p. 145.
24. Bumagin, N.A., Ponomarev, A.V., and Beletskaya, I.P., Zh. Org. Khim., 1987, vol. 23, p. 1354.
25. Wenkert, E., Fernandes, J.B., Vichelotti, T.L., and Swindell, C.S., Synthesis, 1983, vol. 9, p. 701.