Skip to main content
Log in

Synthesis of 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones by reformatsky reaction

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

Abstract

Methyl 1-bromocyclohexanecarboxylate reacted with zinc and aromatic aldehydes in two steps to afford 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones; methyl 1-[aryl(hydroxy)methyl]cyclohexanecarboxylates were also formed as by-products.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Shchepin, V.V., Sazhneva, Yu.Kh., and Kirillov, N.F., Sintez i khimicheskie svoistva zameshchennykh 2,3,5,6-tetragidropiran-2,4-dionov (Synthesis and Chemical Properties of Substituted 2,3,5,6-Tetrahydropyran-2,4-diones), Perm: Perm. Univ., 2007, p. 68.

    Google Scholar 

  2. Melekhin, V.S., Kirillov, N.F., Makhmudov, R.R., and Mardanova, L.G., Vestn. Ural. Med. Akad. Nauki, 2009, vol. 25, no. 2, p. 288.

    Google Scholar 

  3. Kirillov, N.F., Makhmudov, R.R., Gavrilov, A.G., Mardanova, L.G., and Vakhrin, M.I., Pharm. Chem. J., 2013, vol. 47, no. 1, p. 40.

    Article  CAS  Google Scholar 

  4. Kirillov, N.F. and Shchepin, V.V., Russ. J. Org. Chem., 2001, vol. 37, p. 1223.

    Article  CAS  Google Scholar 

  5. Shchepin, V.V., Kirillov, N.F., and Vakhrin, M.I., Russ. J. Gen. Chem., 2004, vol. 74, p. 933.

    Article  CAS  Google Scholar 

  6. Shchepin, V.V., Kirillov, N.F., Melekhin, V.S., and Vakhrin, M.I., Russ. J. Gen. Chem., 2006, vol. 76, p. 1421.

    Article  CAS  Google Scholar 

  7. Kirillov, N.F. and Melekhin, V.S., Russ. J. Gen. Chem., 2009, vol. 79, p. 1707.

    Article  CAS  Google Scholar 

  8. Kirillov, N.F. and Nikiforova, E.A., Russ. J. Org. Chem., 2014, vol. 50, p. 909.

    Article  CAS  Google Scholar 

  9. Hussey, A.S. and Newman, M.S., J. Am. Chem. Soc., 1948, vol. 70, p. 3024.

    Article  CAS  Google Scholar 

  10. Mineno, M., Sawai, Y., Kanno, K., Sawada, N., and Mizufune, H., J. Org. Chem., 2013, vol. 78, p. 5843.

    Article  CAS  Google Scholar 

  11. Unterhalt, B. and Weyrich, K., Arch. Pharm., 1980, vol. 313, p. 795.

    Article  CAS  Google Scholar 

  12. CrysAlisPro, Version 1.171.37.33 (release 27-03-2014 CrysAlis171. NET), Agilent Technologies.

  13. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. F. Kirillov.

Additional information

Original Russian Text © N.F. Kirillov, E.A. Nikiforova, A.N. Vasyanin, M.V. Dmitriev, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 530–534.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kirillov, N.F., Nikiforova, E.A., Vasyanin, A.N. et al. Synthesis of 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones by reformatsky reaction. Russ J Org Chem 51, 513–517 (2015). https://doi.org/10.1134/S1070428015040089

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015040089

Keywords

Navigation