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Synthesis of 1-, 2-Methoxy-, 1,3-Dimethoxyadamantanes And 1-, 4-Methoxydiadamantanes by Reaction of Adamantyl and Diadamantyl Halides with Dimethyl Carbonate in the Presence of Zeolite Catalysts

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Abstract

1-, 2-Methoxy-, 1,3-dimethoxyadamantane, and 1-, 4-methoxydiadamantane were prepared by the reaction of adamantyl and diadamantyl halides with dimethyl carbonate in the presence of zeolite catalysts NiHY or FeHY free of binders. Optimum ratio of catalysts and reagents were found and the reaction conditions for the selective synthesis of methoxyadamantanoids were developed.

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References

  1. Kropp, P.J., Poindexter, G.S., Pienta, N.J., and Hamilton, D.C., J. Am. Chem. Soc., 1976, vol. 98, p. 8135. doi https://doi.org/10.1021/ja00441a043.

    Article  CAS  Google Scholar 

  2. Perkins, R.R. and Pincock, R.E., Tetrahedron Lett., 1975, p. 943. doi https://doi.org/10.1016/S0040-4039(00)72026-0

    Google Scholar 

  3. Kevill, D.N., Kowyck, K.C., and Weite, E.L., J. Am. Chem. Soc., 1970, vol. 92, p. 7300. doi https://doi.org/10.1021/ja00728a012

    Article  CAS  Google Scholar 

  4. Khusnutdinov, R.I., Shchadneva, N.A., Malikov, A.I., and Dzhemilev, U.M., Neftekhimiya, 2000, vol. 40, p. 458.

    CAS  Google Scholar 

  5. Khusnutdinov, R.I., Shchadneva, N.A., and Mayakova, Yu.Yu., Russ. J. Org. Chem., 2014, vol. 50, p. 790. doi https://doi.org/10.1134/S1070428014060050

    Article  CAS  Google Scholar 

  6. Seidl, P.R., Leal, K.Z., and Yoneda, J.D., J. Phys. Org. Chem., 2002, vol. 15, p. 803. doi https://doi.org/10.1002/poc.538

    Article  CAS  Google Scholar 

  7. Inomata, S., Harada, Yu., Matsuoka, Sh., and Ishizone, T., Tetrahedron, 2013, vol. 69, p. 3238. doi https://doi.org/10.1016/j.tet.2013.02.042

    CAS  Google Scholar 

  8. Krishnamurthy, V.V., Shih, J.G., and Olah, G.A., J. Org. Chem., 1985, vol. 50, p. 1161. doi https://doi.org/10.1021/jo00208a003

    Article  CAS  Google Scholar 

  9. Khusnutdinov, R.I., Shchadneva, N.A., Mayakova, Yu.Yu., Yulamanova, A.A., Kazipova, A.N., and Kutepov, B.I., Russ. J. Gen. Chem., 2018, vol. 88, p. 869. doi https://doi.org/10.1134/S1070363218050043

    Article  CAS  Google Scholar 

  10. Kutepov, B.I., Travkina, O.S., Pavlova, I.N., Khazipova, A.N., Grigor’eva, N.G., and Pavlov, M.L., Russ. J. Appl. Chem., 2015, vol. 88, p. 65. doi https://doi.org/10.1134/S1070427215010103

    Article  CAS  Google Scholar 

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Correspondence to Yu. Yu. Mayakova.

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Original Russian Text © R.I. Khusnutdinov, N.A. Shchadneva, Yu.Yu. Mayakova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1710–1712.

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Khusnutdinov, R.I., Shchadneva, N.A. & Mayakova, Y.Y. Synthesis of 1-, 2-Methoxy-, 1,3-Dimethoxyadamantanes And 1-, 4-Methoxydiadamantanes by Reaction of Adamantyl and Diadamantyl Halides with Dimethyl Carbonate in the Presence of Zeolite Catalysts. Russ J Org Chem 54, 1728–1730 (2018). https://doi.org/10.1134/S1070428018110180

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  • DOI: https://doi.org/10.1134/S1070428018110180

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