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Chemical transformations of tetracyclo[3.3.1.1.3,7.0.1,3]decane (1,3-dehydroadamantane): I. Reaction of 1,3-dehydroadamantane with carboxylic acids esters

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Abstract

Adamantylation of carboxylic acids esters was performed with 1,3-dehydroadamantane for the first time. The reaction proceeds under mild conditions and can be used as a convenient single stage procedure for the synthesis of esters of branched carboxylic acids having an adamantyl group in the α-position to the carbonyl group.

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References

  1. Bott, K., Chem. Ber., 1968, vol. 101, p. 564.

    Article  CAS  Google Scholar 

  2. Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516.

    Article  CAS  Google Scholar 

  3. Ohno, M., Itoh, M., Umeda, M., Furuta, R., Kondo, K., and Eguchi, Sh., J. Am. Chem. Soc., 1996, vol. 118, p. 7075.

    Article  CAS  Google Scholar 

  4. Ivleva, E.A., Baimuratov, M.R., Zhuravleva, Yu.A., Klimochkin, Yu.N., Kulikova, I.A., Pozdnyakov, V.V., Sheikina, N.A., Tyshchenko, V.A., and Rudyak, K.B., Pet. Chem., 2015, vol. 55, p. 133.

    Article  CAS  Google Scholar 

  5. Ivleva, E.A., Baimuratov, M.R., Gavrilova, V.S., Zhuravleva, Yu.A., Klimochkin, Yu.N., Kulikova, I.A., Pozdnyakov, V.V., Sheikina, N.A., Tyshchenko, V.A., and Rudyak, K.B., Pet. Chem., 2015, vol. 55, p. 673.

    Article  CAS  Google Scholar 

  6. Reddy, R.P., Lee, G.H., and Davies, H.M.L., Org. Lett., 2006, vol. 8, p. 3437.

    Article  CAS  Google Scholar 

  7. Davies, H.M.L., Hansen, T., and Churchill, M.R., J. Am. Chem. Soc., 2000, vol. 122, p. 3063.

    Article  CAS  Google Scholar 

  8. Pour, M., Spulak, M., Balsanek, V., Kunes, J., Kubanova, P., and Buchta, V., Bioorg. Med. Chem., 2003, vol. 11, p. 2843.

    Article  CAS  Google Scholar 

  9. Reetz, M.T., Schwellnus, K., Huebner, F., Massa, W., and Schmidt, R.E., Chem. Ber., 1983, vol. 116, p. 3708.

    Article  CAS  Google Scholar 

  10. Reetz, M.T. and Schwellnus, K., Tetrahedron Lett., 1978, vol. 17, p. 1455.

    Article  Google Scholar 

  11. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu., Russ. J. Org. Chem., 2002, vol. 38, p. 295.

    Article  CAS  Google Scholar 

  12. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu., Russ. J. Org. Chem., 2003, vol. 39, p. 1668.

    Article  CAS  Google Scholar 

  13. Butov, G.M., Mokhov, V.M., Parshin, G.Yu., Kunaev, R.U., Shevelev, S.A., Dalinger, I.L., and Vatsadze, I.A., Russ. J. Org. Chem., 2008, vol. 44, p. 1157.

    Article  CAS  Google Scholar 

  14. Butov, G.M., Parshin, G.Yu., Kunaev, R.U., and Mokhov, V.M., Izv. VolgGTU, 2007, vol. 5, p. 25.

    Google Scholar 

  15. Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York Wiley–Interscience, 1972; Translated under the title Sputnik khimika, Moscow: Mir, 1976.

    Google Scholar 

  16. Sakakura, A., Koshikari, Y., and Ishihara, K., Tetrahedron Lett., 2008, vol. 49, p. 5017.

    Article  CAS  Google Scholar 

  17. Voelter, W. and Kalbacher, H., Lieb. Ann., 1993, p. 131.

    Google Scholar 

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Authors and Affiliations

  1. Volgograd State Technical University, Volgograd, Russia

    V. M. Mokhov

  2. Volzhskii Polytechnical Institute branch, ul. Engelsa 42A, Volzhskii, 404121, Russia

    V. V. Burmistrov & G. M. Butov

Authors
  1. V. M. Mokhov
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  2. V. V. Burmistrov
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  3. G. M. Butov
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Corresponding author

Correspondence to G. M. Butov.

Additional information

Original Russian Text © V.M. Mokhov, V.V. Burmistrov, G.M. Butov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1128–1130.

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Mokhov, V.M., Burmistrov, V.V. & Butov, G.M. Chemical transformations of tetracyclo[3.3.1.1.3,7.0.1,3]decane (1,3-dehydroadamantane): I. Reaction of 1,3-dehydroadamantane with carboxylic acids esters. Russ J Org Chem 52, 1118–1120 (2016). https://doi.org/10.1134/S1070428016080042

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  • DOI: https://doi.org/10.1134/S1070428016080042

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