Abstract
1-Dimethylamino-3-ferrocenyl-3-oxoprop-1-ene was synthesized by the reaction of acetylferrocene with dimethylformamide dimethyl acetal. Its reactivity in the reactions with mononucleophilic (sodium salts of phenol, thiophenol, benzenesulfinate, diethylphosphorous acid) and binucleophilic reagents (hydrazine hydrate, hydroxylamine, amidines, 1,2-diaminobenzene, 2-aminophenol, 2-aminothiophenol) and methyl iodide was studied. As a result, we obtained new ferrocene-containing α-keto-unsaturated compounds and heterocycles of pyrazole, isoxazole, pyrimidine, and benzazepine series. In the reaction with CH3I formed ferrocenoylacetylene which in the presence of dicarbonyl-bis(triphenylphosphine)nickel catalyst easily trimerized to give a mixture of 1,2,4- and 1,3,5-triferrocenoylbenzene.
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References
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.
Staveren, D.R., and Metzler-Nolte, N., Chem. Rev., 2004, vol. 104, no. 12, p. 5931.
Zora, M. and Gormen, M., J. Organomet. Chem., 2007, vol. 692, no. 22, p. 5026.
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.
Effenberger, F. and Simchen, G., Chem. Ber., 1963, vol. 96, no. 4, p. 1350.
Bredereck, H., Chem. Ber., 1968, vol. 101, no. 1, p. 41.
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.
Ponticello, G.S. and Baldwin, J.J., J. Org. Chem., 1979, vol. 44, no. 14, p. 4003.
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.
Shmushkovich, J., Enaminy (Enamines), in Uspekhi organicheskoi khimii (Advances of Organic Chemistry), Knunyants, I.L., Ed., Moscow: Mir, 1966, vol. 4, pp. 5–123.
Bredereck, H., Sell, R., and Effenberger, F., Chem. Ber., 1964, vol. 97, no. 11, p. 3407.
Dominquez, E., Ibeas, E., Martinez de Marigorta, E., Palacios, J.K., and Saumartin, R., J. Org. Chem., 1996, vol. 61, no. 15, p. 5435.
Schlögl, K. and Monar, A., Monatsh. Chem., 1962, vol. 93, no. 4, p. 861.
Reutov, O.A., Kurts, A.L., and Butin, K.P., Organicheskaya khimiya (Organic Chemistry), Moscow: Mosk. Gos. Univ., 1999, pt. 1, pp. 492–496.
Dzhemilev, U.M., Popod’ko, N.R., and Kozlova, E.V., Metallokompleksnyi kataliz v organicheskom sinteze (Metal Complex Catalysis in Organic Synthesis), Moscow: Khimiya, 1999, pp. 60–61.
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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. 425–432.
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Moskalenko, A.I., Boeva, A.V. & Boev, V.I. Reaction of acetylferrocene with dimethylformamide dimethyl acetal and some transformations of the reaction product. Russ J Gen Chem 81, 521–528 (2011). https://doi.org/10.1134/S1070363211030133
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DOI: https://doi.org/10.1134/S1070363211030133