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A feature of reaction of 1,1′-diacetylferrocene with dimethylformamide dimethyl acetal leading to a new strategy of the synthesis of asymmetrical 1,1′-disubstituted ferrocene

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Abstract

The reaction of 1,1′-diacetylferrocene with the dimethylformamide dimethyl acetal proceeds regioselectively to afford [1-acetyl-1′-(1-dimethylamino-3-oxoprop-1-en-3-yl)]ferrocene, based on which new approaches to the synthesis of 1,1′-disubstituted unsymmetrical ferrocene derivatives via the reaction with nucleophilic reagents hydrazine hydrate, hydroxylamine, and amidines were developed.

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References

  1. Perevalova, E.G., Reshetova, M.D., and Grandberg, K.I., Metody elementoorganicheskoi khimii. Zhelezoorganicheskie soedineniya. Ferrotsen (Methods of Organoelemental Chemistry. Organoiron Compounds. Ferrocene), Moscow: Khimiya, 1983.

    Google Scholar 

  2. Zora, M. and Gormen, M., J. Organomet. Chem., 2007, vol. 692, no. 22, p. 5026.

    Article  CAS  Google Scholar 

  3. Staveren, D.R. and Metzler-Nolte, N., Chem. Rev., 2004, vol. 104, no. 12, p. 5931.

    Article  Google Scholar 

  4. Snegur, L.V., Simenel, A.A., Nekrasov, Yu.S., Morozova, N.V., Peregudova, S.M., Kuzmenko, Yu.V., Babin, V.N., Ostrovskaya, L.A., Bluchterova, N.V., and Fomina, M.M., J. Organomet. Chem., 2004, vol. 689, p. 2473.

    Article  CAS  Google Scholar 

  5. Snegur, L.V., Nekrasov, Yu.S., Sergeeva, N.S., Zhilina, Zh.V., Gumenyuk, V.V., Starikova, Z.A., Simenel, A.A., Morozova, N.V., Sviridova, I.R., and Babin, V.N., Appl. Organometal. Chem., 2008, vol. 22, p. 139.

    Article  CAS  Google Scholar 

  6. Simenel, A.A., Morozova, N.V., Snegur, L.V., Zykova, S.I., Kachala, M.M., Ostrovskaya, L.A., Bluchterova, N.V., and Fomina, M.M., Appl. Organomet. Chem., 2009, vol. 23, p. 219.

    Article  CAS  Google Scholar 

  7. Effenberger, F. and Simchen, G., Chem. Ber., 1963, vol. 96, no. 4, p. 1350.

    Google Scholar 

  8. Bredereck, H., Chem. Ber., 1968, vol. 101, no. 1, p. 41.

    Article  CAS  Google Scholar 

  9. Hengartner, V., Batcho, A.D., Blount, J.F., Leimgruber, W., Larscheid, M.E., and Scott, J.W., J. Org. Chem., 1979, vol. 44, no. 12, p. 3748.

    Article  CAS  Google Scholar 

  10. Ponticello, G.S. and Baldwin, J.J., J. Org. Chem., 1979, vol. 44, no. 14, p. 4003.

    Article  CAS  Google Scholar 

  11. Golyanskaya, O.M., Voloshin, N.A., Chernyshev, A.V., Dubonosov, A.D., Metelitsa, A.V., Mezheritskii, V.V., and Bren’, V.A., Zh. Org. Khim., 2008, vol. 44, no. 4, p. 608.

    Google Scholar 

  12. Shmushkovich, J., Enaminy (Enamines), in Uspekhi organicheskoi khimii (Advances of Organic Chemistry), Knunyants, I.L., Ed., Moscow: Mir, 1966, vol. 4, p. 5.

    Google Scholar 

  13. Bredereck, H., Sell, R., and Effenberger, F., Chem. Ber., 1964, vol. 97, no. 11, p. 3407.

    Article  CAS  Google Scholar 

  14. Dominquez, E., Ibeas, E., Martinez de Marigorta, E., Palacios, J.K., and Saumartin, R., J. Org. Chem., 1996, vol. 61, no. 15, p. 5435.

    Article  Google Scholar 

  15. Boev, V.I. and Dombrovskii, A.V., Zh. Obshch. Khim., 1977, vol. 47, no. 8, p. 1892.

    CAS  Google Scholar 

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Correspondence to A. I. Moskalenko.

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Original Russian Text © A.I. Moskalenko, A.V. Boeva, V.I. Boev, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 3, pp. 433–438.

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Moskalenko, A.I., Boeva, A.V. & Boev, V.I. A feature of reaction of 1,1′-diacetylferrocene with dimethylformamide dimethyl acetal leading to a new strategy of the synthesis of asymmetrical 1,1′-disubstituted ferrocene. Russ J Gen Chem 81, 529–534 (2011). https://doi.org/10.1134/S1070363211030145

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  • DOI: https://doi.org/10.1134/S1070363211030145

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