Skip to main content
SpringerLink
Log in

Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl)methanol epimeric at the C7 atom resulted in scalemic (5R)-5-acetyl-2-methylcyclohex-2-en-1-one.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Corey, E.J. and Suggs, J.W., Tetrahedron Lett., 1975, p. 2647.

  2. Piancatelli, G., Scettri, A., and D’Auria, M., Synthesis, 1982, p. 245.

  3. Sundararaman, P. and Herz, W., J. Org. Chem., 1977, vol. 42, pp. 806, 813.

    Article  CAS  Google Scholar 

  4. Paquette, L.A., Crouse, G.D., and Sharma, A.K., J. Am. Chem. Soc., 1982, vol. 104, p. 4411.

    Article  CAS  Google Scholar 

  5. De Brabander, J., Kulkarni, B.A., Garcia-Lopez, R., and Vandewalle, M., Tetrahedron. Asymmetry., 1997, vol. 8, p. 1721.

    Article  Google Scholar 

  6. Feng, J.-P., Shi, Z.-F., Li, Y., Zhang, J.-T., Qi, X.-L., Chen, J., and Cao, X.-P., J. Org. Chem., 2008, vol. 73, p. 6873.

    Article  CAS  Google Scholar 

  7. Muzart, J., Chem. Rev., 1992, 92, p. 113.

    Article  CAS  Google Scholar 

  8. Wipf, P. and Aslan, D.C., J. Org. Chem., 2001, vol. 66, p. 337.

    Article  CAS  Google Scholar 

  9. Smitt, O. and Högberg, H.-E., Tetrahedron, 2002, vol. 58, p. 7691.

    Article  CAS  Google Scholar 

  10. Chaudhary, S.K., Hernandez, O. Tetrahedron Lett., 1979, p. 99.

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, 450054, Russia

    S. A. Torosyan, F. A. Gimalova, R. F. Valeev & M. S. Miftakhov

Authors
  1. S. A. Torosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. A. Gimalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. F. Valeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Torosyan.

Additional information

Original Russian Text © S.A. Torosyan, F.A. Gimalova, R.F. Valeev, M.S. Miftakhov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 680–684.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Torosyan, S.A., Gimalova, F.A., Valeev, R.F. et al. Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate. Russ J Org Chem 47, 682–686 (2011). https://doi.org/10.1134/S1070428011050058

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011050058

Keywords

Search

Navigation