Russian Journal of Organic Chemistry

, Volume 42, Issue 11, pp 1636–1641 | Cite as

Synthesis of 3-oxatricyclo[4.4.0.02,7]decene derivatives

  • R. N. Zolotarev
  • M. E. Yakovlev
  • V. V. Razin
Article

Abstract

Unsaturated haloethers of norpinane structure were prepared by reaction of N-iodo-and N-bromosuccinimides with 1-phenyltricyclo[4.1.0.02,7]-heptane in the presence of unsaturated propargyl or allyl alcohol. The iodopropargyloxy derivative underwent reductive 6-exo-cyclization when treated with tributyltin hydride resulting in 5-methylene-3-oxa-2-phenyltricyclo[4.4.0.02,7]decane, and the iodoallyloxy derivative on heating in the presence of benzoyl peroxide suffered isomerization into 5-iodomethyl-3-oxa-2-phenyltricyclo[4.4.0.02,7]decene. Bromopropargyloxy and bromoallyloxy derivatives failed to undergo the reductive cyclization under the treatment with a system cobaloxime(III)-sodium borohydride, but suffered hydrogenetion at the multiple carbon-carbon bond.

Keywords

Heptane Sodium Borohydride Benzoyl Peroxide Allyl Alcohol Reductive Cyclization 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Razin, V.V., Zadonskaya, N.Yu., and Makarychev, Yu.A., Zh. Org. Khim., 1990, vol. 26, p. 674; Razin, V.V. and Makarychev, Yu.A., Zh. Org. Khim., 1992, vol. 28, p. 2490; Razin, V.V., Zolotarev, R.N., and Yakovlev, M.E., Zh. Org. Khim., 1998, vol. 34, p. 859; Vasin, V.A., Romanova, E.V., Kostryukov, S.G., and Razin, V.V., Mendeleev Commun., 1998, p. 122; Zolotarev, R.N. and Razin, V.V., Zh. Org. Khim., 1998, vol. 34, p. 1863; Razin, V.V. and Zolotarev, R.N., Zh. Org. Khim., 2003, vol. 39, p. 1782; Zolotarev, R.N. and Razin, V.V., Zh. Org. Khim., 2003, vol. 39, p. 1788.Google Scholar
  2. 2.
    Razin, V.V., Zadonskaya, N.Yu. and Shamurzaev, Kh.T., Zh. Org. Khim., 1991, vol. 27, p. 1253.Google Scholar
  3. 3.
    Razin, V.V., Vasyn, V.A., and Blinkov, I.E., Zh. Org. Khim., 1993, vol. 29, p. 916.Google Scholar
  4. 4.
    Surran, D.P., Synthesis, 1988, p. 417; Jasperse, C.P., Curran, D.P. and Fevig, T.L., Chem. Rev., 1991, vol. 91, p. 1237.Google Scholar
  5. 5.
    Scheffold, R., Rytz, G., and Walder, L., Modern Synthetic Methods, vol. 3, Scheffold, R., Ed., Frankfurt: Diesterweg/Salle, Sauer-lander, 1983, 355 p.; Tada, M. and Okabe, M., Chem. Lett., 1980, p. 201; Okabe, M., Abe, M., and Tada, M., J. Org. Chem., 1982, vol. 47, p. 1775; Torii, S., Inokuchi, T., and Yukawa, T., J. Org. Chem., 1985, vol. 50, p. 5875; Begley, M.J., Landlow, M., and Pattenden, G., J. Chem. Soc., Perkin Trans. 1, 1988, p. 1095.Google Scholar
  6. 6.
    Last, K. and Hoffmann, H.M.R., Synthesis, 1989, p. 901.Google Scholar
  7. 7.
    Neumann, W.P., Synthesis, 1987, p. 665.Google Scholar
  8. 8.
    Curran, D.P., Chen, M.H., and Kim, D., J. Am. Chem. Soc., 1986, vol. 108, p. 2489.CrossRefGoogle Scholar
  9. 9.
    Schrauzer, G.N., Inorg. Synth., 1968, vol. 11, p. 61.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • R. N. Zolotarev
    • 1
  • M. E. Yakovlev
    • 1
  • V. V. Razin
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

Personalised recommendations