Abstract
1,4-Addition of cyanide ion to conjugated nitrosoalkenes of adamantane series, generated in situ from dimers of 2-alkylideneadamantanes nitroso chlorides or from α-chloro-oxime, results in vicinal cyanoximes. Proceeding from the latter approaches to some 2,2-disubstituted adamantanes were developed.
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Vogl, E., Bruns, R., Kretschik, O., Uhr, H., Kaulen, J., Kugler, M., Wachtler, P., Kreiss, W., and Eberz, G., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 625.
Rouchaud, J., Gustin, F., and Moulard, C., Bull. Soc. Chim. Belg., 1993, vol. 102, p. 545.
Gadekar, S.M., Nibi, S., Johnson, B.D., Cohen, E., and Cummings, J.R., J. Med. Chem., 1968, vol. 11, p. 453.
Chiba, S., Hattori, G., and Narasaka, K., Chem. Lett., 2007, vol. 36, p. 52.
Li, X., Du, Y., Liang, Z., Li, X., Pan, Y., and Zhao, K., Org. Lett., 2009, vol. 11, p. 2643.
Swellem, R.H., Allam, Y.A., and Nawwar, A.M., Z. Naturforsch., 1999, vol. 54b, p. 1197.
Martínez, A.G., Vilar, E.T., Fraile, A.G., Cerero, S.M., and Ruiz, P.M., Tetrahedron: Asymm., 1998, vol. 9, p. 1737.
Amer, F.A., Hammouda, M., El-Ahl, A.-A.S., and Abdel-Wahab, B.F., Chem. Heterocycl. Compd., 2007, vol. 43, p. 1559.
Husain, M., Husain, M., Habib, R., and Fazal, A., Indian J. Chem. B., 1986, vol. 25, p. 301.
Komeichi, Y., Iwasaki, T., Ito, Y., and Aida, F., Steroids, 1972, vol. 19, p. 47.
Tilden, W.A. and Burrows, J. Chem. Soc., Trans. 1905, vol. 87, p. 344.
Leach, F.P., J. Chem. Soc., Trans., 1905, vol. 87, p. 413.
Kopranenkov, V.N. and Unkovskii, B.V., Izv. Vuzov. Ser. Khim. i Khim. Tekhnol., 1973, vol. 16, p. 808.
Golovin, E.V., Golovina, O.V., Guseva, G.A., Mal’kova, N.N., and Klimochkin, Yu.N., Izv. Vuzov. Ser. Khim. i Khim. Tekhnol., 2005, vol. 48, p. 65.
Krasnikov, P.E. and Klimochkin, Yu.N., Butlerov. Soobshch., 2012, vol. 31, p. 15.
Golovin, E.V., Krasnikov, P.E., and Klomochkin, Yu.N., Izv. Samar. Nauch. Tsentra Ross. Akad. Nauk, Ser. Khim. I Khim. Technol., 2004, p. 197.
Fritzkow, W., Schaefer, I., Pabst, P., Ebenroth, A., and Beger, J., J. Prakt. Chem., 1965, vol. 29, p. 123.
Krasnikov, P.E., Sidnin, E.A., Osyanin, V.A., and Klimochkin, Yu.N., Chem. Heterocycl. Compd., 2014, vol. 50, p. 1090.
The Chemistry of Hydroxylamines, Oximes and Hydroxamic acids, Rappoport, Z. and Liebman, J.F., Eds., Chichester: Wiley, 2008.
Structure Determination of Organic Compounds, Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Springer-Verlag, Berlin, 2009.
Krasnikov, P.E., Candidate Sci. (Chem.) Dissertation, Samara, 2013.
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Original Russian Text © P.E. Krasnikov, V.A. Osyanin, Yu.N. Klimochkin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 641–644.
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Krasnikov, P.E., Osyanin, V.A. & Klimochkin, Y.N. Synthesis and properties of vicinal cyanoximes of adamantane series. Russ J Org Chem 51, 619–622 (2015). https://doi.org/10.1134/S107042801505005X
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DOI: https://doi.org/10.1134/S107042801505005X