Advertisement

Russian Journal of Organic Chemistry

, Volume 40, Issue 7, pp 966–972 | Cite as

Degenerate Rearrangement of Long-Lived 9,10-Dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium Ion: 1,2-Shift of the Dimethylvinyl Group

  • V. A. Bushmelev
  • A. M. Genaev
  • V. G. Shubin
Article

Abstract

Dynamic NMR study showed that 9,10-dimethyl-9-(cis-1-methyl-1-propenyl)phenanthrenium ion generated by reaction of 1,2,2a,10b-tetramethyl-2a,10b-dihydrocyclobuta[l]phenanthrene with HSO3F below -100°C undergoes very fast (ΔG = 22 kJ/mol at -120°C ) degenerate 1,2-shift of the dimethylvinyl group.

Keywords

Organic Chemistry Phenanthrene HSO3F Degenerate Rearrangement 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Bushmelev, V.A., Genaev, A.M., and Shubin, V.G., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 1373.Google Scholar
  2. 2.
    Koptyug, V.A., Carbkationy: Stroenie i reaktsionnaya sposobnost'. Izbrannye trudy(Carbocations: Structure and Reactivity. Selected Works), Moscow: Nauka, 2001-2002, vol. 1.Google Scholar
  3. 3.
    Stiles, M. and Mayer, R.P., J. Am. Chem. Soc., 1959, vol. 81, p. 1497.Google Scholar
  4. 4.
    Koptyug, V.A., Arenonievye iony. Stroenie i reaktsion-naya sposobnost'(Arenonium Ions. Structure and Reac-tivity), Novosibirsk: Nauka, 1983.Google Scholar
  5. 5.
    Borodkin, G.I. and Shubin, V.G., Chemistry Rev., 1999, vol. 24, part 2, p. 1; Borodkin, G.I. and Shubin, V.G., Usp. Khim., 1995, vol. 64, p. 672.Google Scholar
  6. 6.
    Hart, H. and Kuzuya, M., J. Am. Chem. Soc., 1973, vol. 95, p. 4096.Google Scholar
  7. 7.
    Hart, H. and Kuzuya, M., J. Am. Chem. Soc., 1975, vol. 97, p. 2459.Google Scholar
  8. 8.
    Nisnevich, G.A., Vyalkov, A.I., Kamshii, G.T., Mamatyuk, V.I., and Barkhash, V.A., Zh. Org. Khim., 1983, vol. 19, p. 2081.Google Scholar
  9. 9.
    Mayr, H. and Olah, G.A., J. Am. Chem. Soc., 1977, vol. 99, p. 510.Google Scholar
  10. 10.
    Zefirov, N.S., Davydova, A.F., and Yur'ev, Yu.K., Zh. Obshch. Khim., 1966, vol. 36, p. 1217; Thomas, A.F., J. Chem. Soc., Chem. Commun., 1970, p. 1054; Bly, R.S. and Swindell, R.T., J. Org. Chem., 1965, vol. 30, p. 10; Miller, J.A. and Ullah, G.M., J. Chem. Soc., Chem. Commun., 1982, p. 874.Google Scholar
  11. 11.
    Shubin, V.G., Korchagina, D.V., Borodkin, G.I., Derendyaev, B.G., and Koptyug, V.A., Zh. Org. Khim., 1973, vol. 9, p. 1031; Shubin, V.G., Korchagina, D.V., Deren-dyaev, B.G., Borodkin, G.I., and Koptyug, V.A., Zh. Org. Khim., 1973, vol. 9, p. 1041.Google Scholar
  12. 12.
    Bushmelev, V.A., Genaev, A.M., Osadchii, S.A., Shakirov, M.M., and Shubin, V.G., Russ. J. Org. Chem., 2003, vol. 39, p. 1301.Google Scholar
  13. 13.
    Osadchii, S.A., Drobysh, V.A., Mikushova, N.V., and Shubin, V.G., Zh. Org. Khim., 1989, vol. 25, p. 1838.Google Scholar
  14. 14.
    Woodward, R.B. and Hoffmann, R., The Conservation of Orbital Symmetry, New York: Academic, 1970; Lehr, R.E. and Marchand A.P., Orbital Symmetry. A Problem-Solving Approach, New York: Academic, 1972.Google Scholar
  15. 15.
    Bushmelev, V.A., Shakirov, M.M., Derendyaev, B.G., and Koptyug, V.A., Zh. Org. Khim., 1979, vol. 15, p. 1934.Google Scholar
  16. 16.
    Rezvukhin, A.I., Korchagina, D.V., and Shubin, V.G., Izv. Akad. Nauk SSSR, Ser. Khim., 1976, p. 1253.Google Scholar
  17. 17.
    Korchagina, D.V., Derendyaev, B.G., Shubin, V.G., and Koptyug, V.A., Zh. Org. Khim., 1971, vol. 7, p. 2582.Google Scholar
  18. 18.
    Woyski, M.M., J. Am. Chem. Soc., 1950, vol. 72, p. 919.Google Scholar
  19. 19.
    Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S.J., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347; http://www.msg.ameslab.gov/ GAMESS/GAMESS.html.Google Scholar
  20. 20.
    Kutzelnigg, W., Fleischer, U., and Schingler, M., NMR Basis Principles and Progress, Diehl, P., Fluck, E., Gü</del>ünter, H., Kosfeld, R., and Seelig, J., Eds., Berlin: Springer, 1991, vol. 23, p. 165.Google Scholar
  21. 21.
    Helgaker, T., Jensen, H.J.A., Jørgensen, P., Olsen, J., Ruud, K., Ågren, H., Auer, A.A., Bak, K.L., Bakken, V., Christiansen, O., Coriani, S., Dahle, P., Dalskov, E.K., Enevoldsen, T., Fernandez, B., Hüttig, C., Hald, K., Halkier, A., Heiberg, H., Hettema, H., Jonsson, D., Kirpekar, S., Kobayashi, R., Koch, H., Mikkelsen, K.V., Norman, P., Packer, M.J., Pedersen, T.B., Ruden, T.A., Sanchez, A., Saue, T., Sauer, S.P.A., Schimmelpfenning, B., Sylvester-Hvid, K.O., Taylor, P.R., and Vahtras, O., DALTON, a Molecular Electronic Structure Program, Release 1.2, 2001; http://www.kjemi.uio.no/ software/dalton/dalton.html.Google Scholar
  22. 22.
    Bain, A.D. and Duns, G.J., Can. J. Chem., 1996, vol. 74, p. 819; http://www.chemistry.mcmaster.ca/ ~bain/mexmanc.html.Google Scholar
  23. 23.
    Rybalova, T.V., Gatilov, Yu.V., Kochubei, N.V., Osadchii, S.A., and Shubin, V.G., Zh. Strukt. Khim., 1997, vol. 38, p. 1140.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2004

Authors and Affiliations

  • V. A. Bushmelev
  • A. M. Genaev
  • V. G. Shubin

There are no affiliations available

Personalised recommendations