Abstract
According to the results of PBE0/cc-pVTZ quantum chemical calculations, the equilibrium mixture of α-diazocarbonyl bullvalene derivatives (C10H8N2O) contains an impurity of the corresponding bullvaleno-[1,2,3]oxadiazoles. The carbonyl group in the major tautomer is conjugated with the three-membered ring. The concentration of other tautomers in the equilibrium mixture of two bullvaleno[1,2,3]selenadiazoles is negligible.
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Schröder, G., Oth, J.F.M., and Merenyi, R., Angew. Chem., Int. Ed. Engl., 1965, vol. 4, p. 752.
Semenov, S.G. and Makarova, M.V., Russ. J. Gen. Chem., 2012, vol. 82, p. 1527.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision B.05, Wallingford CT: Gaussian, 2004.
Schulz, R. and Schweig, A., Angew. Chem., Int. Ed. Engl., 1979, vol. 18, p. 692; Schulz, R. and Schweig, A., Angew. Chem., Int. Ed. Engl., 1984, vol. 23, p. 509.
Semenov, S.G. and Sigolaev, Yu.F., Zh. Strukt. Khim., 2004, vol. 45, p. 1128.
Semenov, S.G. and Makarova, M.V., Russ. J. Gen. Chem., 2011, vol. 81, p. 1555.
Schaller, R.J., Gleiter, R., Hofmann, J., and Rominger, F., Angew. Chem., Int. Ed., 2002, vol. 41, p. 1181.
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Original Russian Text © S.G. Semenov, M.V. Makarova, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 3, pp. 450–452.
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Semenov, S.G., Makarova, M.V. Quantum chemical study of α-diazocarbonyl bullvalene derivatives and related heterocyclic compounds. Russ J Org Chem 50, 439–441 (2014). https://doi.org/10.1134/S1070428014030245
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DOI: https://doi.org/10.1134/S1070428014030245