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Benzene Alkylation with Cycloolefins under the Action of [Et3NH]+[Al2Cl7]− Ionic Liquid

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Abstract

Benzene alkylation with mono- and bicyclic olefins under the action of an inorganic ionic liquid [Et3NH]+[Al2Cl7]− with the formation of benzene cycloalkyl derivatives in 58–98% yield has been performed for the first time. It has been found that the increase in the olefin cycle size improves the selectivity with respect to monocycloalkyl derivatives.

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References

  1. Koch, V.R., Miller, L.L., and Osteryoung, R.A., J. Am. Chem. Soc., 1976, vol. 98, p. 5277. https://doi.org/10.1021/ja00433a037

    Article  CAS  Google Scholar 

  2. Qiao, K. and Deng, Y., J. Mol. Catal. (A), 2001, vol. 17, p. 81. https://doi.org/10.1016/s1381-1169(01)00107-8

    Article  Google Scholar 

  3. Wilkes, J.S., Frye, J.S., and Reynolds, G.F., Inorg. Chem., 1983, vol. 22, p. 3870. https://doi.org/10.1021/ic00168a011

    Article  CAS  Google Scholar 

  4. Xin, H., Wu, Q., Han, M., Wang, D., and Jin, Y., Appl. Catal. (A), 2005, vol. 292, p. 354. https://doi.org/10.1016/j.apcata.2005.06.012

    Article  CAS  Google Scholar 

  5. Sun, X.W. and Thao, S.Q., Pet. Sci., 2011, vol. 8, p. 495. https://doi.org/10.1007/s12182-011-0167-4

    Article  CAS  Google Scholar 

  6. Kim, D.S. and Ahn, W.S., Korean J. Chem. Eng., 2003, vol. 20, p. 39. https://doi.org/10.1007/bf02697182

    Article  CAS  Google Scholar 

  7. Boon, J.A., Levisky, J.A., Pflug, J.L., and Wilkes, J.S., J. Org. Chem., 1986, vol. 51, p. 480. https://doi.org/10.1021/jo00354a013

    Article  CAS  Google Scholar 

  8. Adams, C.J., Earle, M.J., and Seddon, K.R., Chem. Commun., 1998, p. 2097. https://doi.org/10.1039/a805599h

  9. Xin-hua, Y., Min, C., Qi-xun, D., and Xiao-nong, C., Chem. Eng. J., 2009, vol. 146, p. 266. https://doi.org/10.1016/j.cej.2008.09.022

    Article  Google Scholar 

  10. Zavgorodnii, S.V., Ovchinnikov, VG., Ovchinnikova, G.K., Mramornova, S.A., and Bass, S.I., Neftekhim., 1972, vol. 12, p. 201.

    Google Scholar 

  11. Karshtedt, D., Bell, A.T., and Tilley, T.D., Organometallics, 2004, vol. 18, p. 4169. https://doi.org/10.1021/om0495325

    Article  Google Scholar 

  12. Qiao, K. and Yokoyama, C., Chem. Lett., 2004, vol. 33, p. 472. https://doi.org/10.1246/cl.2004.472

    Article  CAS  Google Scholar 

  13. Singh, R.P., Kamble, R.M., Chandra, K.L., Saravanan, P., and Singh, V.K., Tetrahedron, 2001, vol. 57, p. 241. https://doi.org/10.1016/s0040-4020(00)01005-x

    Article  CAS  Google Scholar 

  14. Fang, M.-H. and Wang, L.-S., Int. J. Mol. Sci., 2007, vol. 8, p. 470. https://doi.org/10.3390/i8060470

    Article  CAS  Google Scholar 

  15. Kumara, R., Kumarb, A., and Khannab, A., Catal. Ind., 2015, vol. 7, p. 188. https://doi.org/10.1134/S2070050415030095

    Article  Google Scholar 

  16. Bedford, R.B., Brenner, P.B., Carter, E., Carvell, T.W., Cogswel, P.M., Gallagher, T., and Pye, D.R., Chem. — A Eur. J., 2014, vol. 20, p. 7935. https://doi.org/10.1002/chem.201402174

    Article  CAS  Google Scholar 

  17. Salvi, L., Davis, N.R., Ali, S.Z., and Buchwald, S.L., Org. Lett., 2011, vol. 14, p. 170. https://doi.org/10.1021/o1202955h

    Article  Google Scholar 

  18. Kloppenburg, L., Jones, D., and Bunz, U.H.F., Macromol., 1999, vol. 32, p. 4194. https://doi.org/10.1021/ma9900535

    Article  CAS  Google Scholar 

  19. Powell, D.A. and Fu, G.C., J. Am. Chem. Soc., 2004, vol. 126, p. 7788. https://doi.org/10.1021/ja047433c

    Article  CAS  Google Scholar 

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Funding

This study was financially supported by the Russian Foundation for Basic Research (no. 17-43-020155 r_a) in the scope of the State Task of the Ministry of Education and Science (no. AAAA-A19-119022290009-3) and the Program for Support of Young Russian Scientists — Scholarship from the President of Russian Federation (SP-1601.2018.1). The study of the structure of the synthesized compounds was performed using the equipment of “Agidel” Regional Center for Collective Usage (Institute of Petrochemistry and Catalysis, Russian Academy of Sciences).

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences, Ufa, 450075, Russia

    R. I. Aminov, A. S. Mazitova & R. I. Khusnutdinov

Authors
  1. R. I. Aminov
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  2. A. S. Mazitova
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  3. R. I. Khusnutdinov
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Corresponding author

Correspondence to R. I. Aminov.

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Conflict of Interest

No conflict of interest was declared by the authors.

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 11, pp. 1643–1650.

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Aminov, R.I., Mazitova, A.S. & Khusnutdinov, R.I. Benzene Alkylation with Cycloolefins under the Action of [Et3NH]+[Al2Cl7]− Ionic Liquid. Russ J Gen Chem 89, 2171–2177 (2019). https://doi.org/10.1134/S107036321911001X

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  • DOI: https://doi.org/10.1134/S107036321911001X

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