Skip to main content
SpringerLink
Log in

Nitrochlorination of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone

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

Abstract

Treatment of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone with a ∼1:8 mixture of N2O4 and NOCl in diethyl ether at −5 to 0°C gave products of formal anti-addition of NO2Cl at the central C1-C7 bond. In the reaction with phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone nitryl chloride acts as an effective chlorinating agent; as a result, a mixture of diastereoisomeric syn- and anti-6,7-dichlorobicyclo[3.1.1]hept-6-yl phenyl sulfones at a ratio of 7.5:1 is formed.

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. Vasin, V.A., Kostryukov, S.G., Bolusheva, I.Yu., and Razin, V.V., Russ. J. Org. Chem., 2008, vol. 44, p. 511.

    Article  CAS  Google Scholar 

  2. Bräuer, G., Handbuch der präparativen anorganischen Chemie, Stuttgart: Enke, 1981.

    Google Scholar 

  3. Karyakin, Yu.V. and Angelov, I.I., Chistye khimicheskie veshchestva (Pure Chemicals), Moscow: Khimiya, 1974, p. 21.

    Google Scholar 

  4. Brown, D.W., J. Chem. Educ., 1985, vol. 62, p. 209.

    Article  CAS  Google Scholar 

  5. Wiberg, K.B. and Hess, B.A., J. Org. Chem., 1966, vol. 31, p. 2250.

    Article  CAS  Google Scholar 

  6. O’Bannon, P.E. and Dailey, W.P., Tetrahedron, 1990, vol. 46, p. 7341.

    Article  CAS  Google Scholar 

  7. Kadzyauskas, P.P. and Zefirov, N.S., Usp. Khim., 1968, vol. 37, p. 1243.

    Google Scholar 

  8. Vasin, V.A., Kostryukov, S.G., and Razin, V.V., Russ. J. Org. Chem., 1998, vol. 34, p. 1136.

    CAS  Google Scholar 

  9. Borbulevych, O.Ya., Semenov, A.V., Vasin, V.A., and Razin, V.V., Acta Crystallogr., Sect. E, 2002, vol. 58, p. 925.

    Article  CAS  Google Scholar 

  10. Vasin, V.A., Bolusheva, I.Yu., Surmina, L.S., Buevich, A.V., Sergeev, N.M., Tanaseichuk, B.S., and Zefirov, N.S., Zh. Org. Khim., 1990, vol. 26, p. 1501.

    CAS  Google Scholar 

  11. Christl, M., Advances in Strain in Organic Chemistry, Greenwich: JAI, 1995, vol. 4, p. 163.

    Google Scholar 

  12. Wiberg, K.B. and Szeimies, G., J. Am. Chem. Soc., 1970, vol. 92, p. 571.

    Article  CAS  Google Scholar 

  13. Beger, J., J. Prakt. Chem., 1967, vol. 35, p. 326; Zyk, N.V., Bondarenko, O.B., Nesterov, E.E., and Zefirov, N.S., Russ. J. Org. Chem., 1999, vol. 35, p. 980.

    Article  CAS  Google Scholar 

  14. Razin, V.V., Eremenko, M.V., and Ogloblin, K.A., Zh. Org. Khim., 1978, vol. 14, p. 973.

    CAS  Google Scholar 

  15. Vasin, V.A., Bolusheva, I.Yu., Chernyaeva, L.V., Tanaseichuk, B.S., Surmina, L.S., and Zefirov, N.S., Zh. Org. Khim., 1990, vol. 26, p. 1509.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ogarev Mordovian State University, ul. Bol’shevistskaya 68, Saransk, 430000, Russia

    V. A. Vasin, S. G. Kostryukov & A. V. Semenov

  2. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    V. V. Razin

Authors
  1. V. A. Vasin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Kostryukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Razin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Vasin.

Additional information

Original Russian Text © V.A. Vasin, S.G. Kostryukov, A.V. Semenov, V.V. Razin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 533–536.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vasin, V.A., Kostryukov, S.G., Semenov, A.V. et al. Nitrochlorination of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate and phenyl tricyclo[4.1.0.02,7]hept-1-yl sulfone. Russ J Org Chem 44, 528–531 (2008). https://doi.org/10.1134/S1070428008040106

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008040106

Keywords

Search

Navigation