Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 825–828 | Cite as

Reaction of Styrene with Chlorine Dioxide

  • I. V. Loginova
  • I. Yu. Chukicheva
  • A. V. Kuchin
Letters to the Editor
  • 8 Downloads

Abstract

Reaction of styrene with chlorine dioxide under various conditions selectively produces 1-phenyl- 2-chloroethanone, with 1-phenyl-2-chloroethanol, 2-hydroxy-1-phenylethanone, (1,2-dichloroethyl)benzene, (2-chloro-1-phenyl)ethene, and (1,2,2-trichloroethyl)benzene isolated as reaction byproducts.

Keywords

1-phenyl-2-chloroethanone 1-phenyl-2-chloroethanol 2-hydroxy-1-phenylethanone (1,2-dichloroethyl) benzene (2-chloro-1-phenyl)ethene (1,2,2-trichloroethyl)benzene 

Notes

Acknowledgments

The research done using the equipment of Center for Collective Use “Khimiya” of Russian Academy of Sciences, Ural Branch, Komi Science Centre, Institute of Chemistry.

References

  1. 1.
    Ohkuma, T., Tsutsumi, T., Utsumi, N., Arai, N., Noyori, R., and Murata, K., Org. Lett., 2007, vol. 9, no. 2, p. 255. doi 10.1021/ol062661sCrossRefGoogle Scholar
  2. 2.
    Khimicheskaya entsiklopediya (Chemical Encyclopedia), Zefirov, N.S., Ed., Moscow: Bol’shaya Rossiiskaya Entsiklopediya, 1992, vol. 3, p. 347.Google Scholar
  3. 3.
    Lohs, K., Synthetische Gifte. Chemie, Wirkung und militärische Bedeutung: ein Überblick, Berlin (Ost): Ministerium für nationale Verteidigung, 1958.Google Scholar
  4. 4.
    USSR Patent 118261, 1958.Google Scholar
  5. 5.
    Metody polucheniya khimicheskikh reaktivov i preparatov (Methods of Obtaining Chemical Reagents and Preparations), Moscow: NIITEKhIM, 1970, issue 21, p. 50.Google Scholar
  6. 6.
    Kutchin, A.V., Frolova, L.L., and Dreval, I.V., Russ. Chem. Bull., 1996, no. 7, p. 1782.Google Scholar
  7. 7.
    Frolova, L.L., Popov, A.V., Bezuglaja, L.V., Alekseev, I.N., Slepukhin, P.A., and Kutchin, A.V., Russ. J. Gеn. Сhеm., 2014, vol. 84, no. 5, p. 853. doi 10.1134/S1070363214050120Google Scholar
  8. 8.
    Loginova, I.V., Rubtsova, S.A., and Kuchin, A.V., Chem. Nat. Compd., 2008, vol. 44, no. 6, p. 752. doi 10.1007/s10600-009-9182-8CrossRefGoogle Scholar
  9. 9.
    Lezina, O.M., Grebenkina, O.N., Sudarikov, D.V., Krymskaya, Yu.V., Rubtsova, S.A., and Kutchin, A.V., Russ. J. Org. Chem., 2015, vol. 51, no. 10, p. 1359. doi 10.1134/S1070428015100012CrossRefGoogle Scholar
  10. 10.
    Izmest’ev, E.S., Lezina, O.M., Grebyonkina, O.N., Patov, S.A., Rubtsova, S.A., and Kutchin, A.V., Russ. Chem. Bull., 2014, no. 9, p. 2067. doi 10.1007/s11172-014-0702-8CrossRefGoogle Scholar
  11. 11.
    Loginova, I.V., Ashikhmina, E.V., Rubtsova, S.A., Krymskaya, Yu.V., and Kutchin, A.V., Russ. J. Org. Chem., 2008, vol. 44, no. 12, p. 1773. doi 10.1134/S1070428008120087CrossRefGoogle Scholar
  12. 12.
    Loginova, I.V., Rodygin, K.S., Rubtsova, S.A., Slepukhin, P.A., Kutchin, A.V., and Polukeev, V.A., Russ. J. Org. Chem., 2011, vol. 47, no. 1, p. 124. doi 10.1134/S1070428011010167CrossRefGoogle Scholar
  13. 13.
    Krymskaya, Yu.V., Loginova, I.V., Rubtsova, S.A., and Kutchin, A.V., Russ. J. Org. Chem., 2013, vol. 49, no. 2, p. 215. doi 10.1134/S107042801302005XCrossRefGoogle Scholar
  14. 14.
    Nam, K.C. and Kim, J.M., Bull. Korean Chem. Soc., 1994, vol. 15, p. 268.Google Scholar
  15. 15.
    Ganiev, I.M., Ganieva, E.S., and Kabalnova, N.N., Russ. Chem. Bull., 2004, vol. 53, no. 10, p. 2281. doi 10.1007/s11172-005-0114-xCrossRefGoogle Scholar
  16. 16.
    Loginova, I.V., Chukicheva, I.V., and Kutchin, I.V., Russ. J. Org. Chem., 2011, vol. 47, no. 10, p. 1501. doi 10.1134/S1070428011100083CrossRefGoogle Scholar
  17. 17.
    Fredricks, P.S., Lindgren, B.O., and Theander, O., Acta Chem. Scand., 1970, vol. 24, p. 736. doi 10.3891/acta.chem.scand.24-0736CrossRefGoogle Scholar
  18. 18.
    Lindgren, B.O. and Nilsson, T., Acta Chem. Scand. B, 1974, vol. 28, p. 847. doi 10.3891/acta.chem.scand.28b-0847CrossRefGoogle Scholar
  19. 19.
    Kolar, J.J. and Lindgren, B.O., Acta Chem. Scand. B, 1982, vol. 36, p. 599. doi 10.3891/acta.chem.scand.36b-0599CrossRefGoogle Scholar
  20. 20.
    Cherches, B.Kh., Shunkevich, A.A., Belotserkovskya, T.N., and Egiaszarov, Yu.G., Zh. Prikl. Khim., 1999, vol. 72, no. 4, p. 623.Google Scholar
  21. 21.
    Egiazarov, Yu.G., Potapova, L.L, Radkevich, V.Z., Soldatov, V.S., Shunkevich, A.A., and Cherches, B.Kh., Khim. Inter. Ustoich. Razv., 2001, no. 3, p. 417.Google Scholar
  22. 22.
    Michaelson, R.C, Palermo, R.E., and Sharpless, K.C., J. Am. Chem. Soc., 1977, vol. 99, no. 6, p. 1990. doi 10.1021/ja00448a059CrossRefGoogle Scholar
  23. 23.
    Holland, H.L. and Thomas, E.M., Can. J. Chem., 1979, vol. 57, p. 3069.CrossRefGoogle Scholar
  24. 24.
    Şenocak, E., Taşkesenligil, Y., Tűmer, F., and Kazaz, C., Turk. J. Chem., 2005, vol. 29, p. 679.Google Scholar
  25. 25.
    Gamble, M.P. and Smith, A.R.C., J. Org. Chem., 1998, vol. 63, p. 6068. doi 10.1021/jo980674gCrossRefGoogle Scholar
  26. 26.
    Plietker, B., J. Org. Chem., 2004, vol. 69, p. 8287. doi 10.1021/jo048822sCrossRefGoogle Scholar
  27. 27.
    Miller, R.B. and McGarvey, G., J. Org. Chem., 1978, vol. 43, p. 4424. doi 10.1021/jo00417a006CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • I. V. Loginova
    • 1
  • I. Yu. Chukicheva
    • 1
  • A. V. Kuchin
    • 1
  1. 1.Institute of Chemistry, Komi Scientific Center, Ural BranchRussian Academy of SciencesSyktyvkar, Komi RepublicRussia

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