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Quantum chemical simulation of 1,3-dipolar cycloaddition of nitrones to alkenes and their (η6-arene)(tricarbonyl)-chromium complexes

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Abstract

Charge distribution and frontier orbital energies of styrene, C,N-diphenylnitrone, and their (arene)-(tricarbonyl)chromium complexes were calculated by quantum chemical methods. The difference in the HOMO and LUMO energies of the chromium complexes was found to be smaller than in the free ligands, and the reactions with (arene)(tricarbonyl)chromium complexes were characterized by higher rate and selectivity.

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References

  1. Gilchrist, T.L., Heterocyclic Chemistry, Harlow, Essex, England: Longman Scientific & Technical, 1992, 2nd ed. Translated under the title Khimiya geterotsiklov, Moscow: Mir, 1996, p. 111.

    Google Scholar 

  2. Gothelf, K.V. and Jørgensen, K.A., Chem. Rev., 1998, vol. 98, p. 863; Gothelf, K.V. and Jørgensen, K.A., Chem. Commun., 2000, p. 1449; Confalone, P.N. and Huie, E.M., Org. React., 1988, vol. 36, p. 1; Nguyen, T.B., Martel, A., Dhal, R., and Dujardin, G., J. Org. Chem., 2008, vol. 73, p. 2621.

    Article  CAS  Google Scholar 

  3. Artemov, A.N., Sazonova, E.V., Mavrina, E.A., and Zarovkina, N.Yu., Russ. Chem. Bull., Int. Ed., 2012, vol. 61, no. 11, p. 2076.

    Article  CAS  Google Scholar 

  4. Artemov, A.N., Sazonova, E.V., and Zarovkina, N.Yu., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, no. 6, p. 1382.

    Article  CAS  Google Scholar 

  5. Mukai, C., Kim, I.J., Cho, W.J., Kido, M., and Hanaoka, M., J. Chem. Soc., Perkin Trans. 1, 1993, p. 2495.

    Google Scholar 

  6. Mukai, C., Kim, I.J., Cho, W.J., and Hanaoka, M., Tetrahedron Lett., 1990, vol. 31, p. 6893.

    Article  CAS  Google Scholar 

  7. Houk, K.N., Bimanand, A., Mukherjee, D., Sims, J., Chang, Y.-M., Kaufman, D.S., and Domelsmith, L.N., Heterocycles, 1977, vol. 7, p. 293.

    Article  CAS  Google Scholar 

  8. Woodward, R.B. and Hoffman, R., J. Am. Chem. Soc., 1965, vol. 87, p. 395.

    Article  CAS  Google Scholar 

  9. Woodward, R.B. and Hoffmann, R., The Conservation of Orbital Symmetry, New York: Academic, 1970. Translated under the title Sokhranenie orbital’noi simmetrii, Moscow: Mir, 1971, p. 16.

    Google Scholar 

  10. Huisgen, R., Grashey, R., Hawk, H., and Seidl, H., Chem. Ber., 1968, vol. 101, p. 2548.

    Article  CAS  Google Scholar 

  11. Sustmann, R., Tetrahedron Lett., 1971, vol. 12, no. 29, p. 2717.

    Article  Google Scholar 

  12. Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Jr., Organic Solvents: Physical Properties and Methods of Purification, New York: Intersci., 1955, 2nd ed.

    Google Scholar 

  13. Raush, M.D., Moser, G.A., Zaiko, E.S., and Lipman, A.L., J. Organomet. Chem., 1970, vol. 23, p. 185.

    Article  Google Scholar 

  14. Heusler, K., Wieland, P., and Meystre, Ch., Organic Syntheses, Baumgarten, H. E., Ed., New York: Wiley, 1973, collect. vol. 5, p. 1124.

  15. Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, p. 209.

    CAS  Google Scholar 

  16. Hohenberg, P. and Kohn, W., Phys. Rev. B, 1964, vol. 136, p. 864.

    Article  Google Scholar 

  17. Kohn, W. and Sham, L.J., Phys. Rev. A, 1965, vol. 140, p. 1133.

    Article  Google Scholar 

  18. Becke, A.D., Phys. Rev. A, 1988, vol. 38, p. 3098.

    Article  CAS  Google Scholar 

  19. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785.

    Article  CAS  Google Scholar 

  20. Hay, P.J. and Wadt, W.R., J. Chem. Phys., 1985, vol. 82, p. 270.

    CAS  Google Scholar 

  21. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., 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., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision A.1, Wallingford CT: Gaussian, 2009.

    Google Scholar 

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Authors and Affiliations

  1. Lobachevsky State University of Nizhni Novgorod, pr. Gagarina 23-5, Nizhni Novgorod, 603950, Russia

    N. Yu. Zarovkina, E. V. Sazonova & A. N. Artemov

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  1. N. Yu. Zarovkina
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  2. E. V. Sazonova
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  3. A. N. Artemov
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Correspondence to N. Yu. Zarovkina.

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Original Russian Text © N.Yu. Zarovkina, E.V. Sazonova, A.N. Artemov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 1044–1048.

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Zarovkina, N.Y., Sazonova, E.V. & Artemov, A.N. Quantum chemical simulation of 1,3-dipolar cycloaddition of nitrones to alkenes and their (η6-arene)(tricarbonyl)-chromium complexes. Russ J Org Chem 50, 1028–1032 (2014). https://doi.org/10.1134/S1070428014070161

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  • DOI: https://doi.org/10.1134/S1070428014070161

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