Skip to main content
SpringerLink
Log in

Thermal decomposition products of methyl 1,5-diphenyl- and 5-methyl-1-phenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-exo-carboxylates

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

Abstract

Methyl 1,5-diphenyl- and 5-methyl-1-phenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-exo-carboxylates at 138°C undergo decomposition via elimination of nitrogen molecule with formation in each case of five products. Two products are methyl 1,3-diphenyl(or 1-methyl-3-phenyl)bicyclo[1.1.0]butane-2-endo- and -exo-carboxylates, and the three others are derivatives of buta-1,3-diene, methyl (Z)-2-benzylidene-3-phenyl(or 3-methyl)but-3-enoate and methyl (E)- and (Z)-3,4-diphenyl(or 4-methyl-3-phenyl)penta-2,4-dienoates. The formation of these products may be rationalized assuming intermediacy of substituted allylcarbene which undergoes both intramolecular cycloaddition and rearrangements involving 1,2-hydride and 1,2-vinyl shifts.

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. Eaton, D.F., Bergman, R.G., and Hammond, G.J., J. Am. Chem. Soc., 1972, vol. 94, p. 1351.

    Article  Google Scholar 

  2. Komendantov, M.I., Bekmukhametov, R.R., and Novinskii, V.G., Zh. Org. Khim., 1976, vol. 12, p. 801.

    CAS  Google Scholar 

  3. Schneider, M. and Csacsko, B., Angew. Chem., Int. Ed. Engl., 1977, vol. 16, p. 867.

    Article  Google Scholar 

  4. Regitz, M., Welter, W., and Hartman, A., Chem. Ber., 1979, vol. 112, p. 2509.

    Article  CAS  Google Scholar 

  5. Guiborel, C., Danion-Bougot, R., Danion, D., and Carrie, R., Tetrahedron Lett., 1981, p. 441.

    Google Scholar 

  6. Padwa, A., Kumagai, T., and Tohidi, M., J. Org. Chem., 1983, vol. 48, p. 1834.

    Article  CAS  Google Scholar 

  7. Bushby, R.J. and Jusudason, M.V., J. Chem. Res. M., 1986, p. 1144.

    Google Scholar 

  8. Kuznetsov, M.A., Kuchuk, I.D., and Gindin, V.A., Russ. J. Org. Chem., 1997, vol. 33, p. 1507.

    CAS  Google Scholar 

  9. Razin, V.V., Yakovlev, M.E., Shataev, K.V., and Selivanov, S.I., Russ. J. Org. Chem., 2004, vol. 40, p. 1027.

    Article  CAS  Google Scholar 

  10. Masamune, S., Tetrahedron Lett., 1965, vol. 6, p. 945.

    Article  Google Scholar 

  11. Razin, V.V., Petrov, P.S., and Vasin, V.A., Russ. J. Org. Chem., 2012, vol. 48, p. 1041.

    Article  CAS  Google Scholar 

  12. Barfield, M. and Chakrabarti, B., Chem. Rev., 1969, vol. 69, p. 757.

    Article  CAS  Google Scholar 

  13. Padwa, A. and Kennedy, G.D., J. Org. Chem., 1984, vol. 49, p. 4344.

    Article  CAS  Google Scholar 

  14. Frank-Neuman, M., Dietrich-Buchecker, C., and Khemiss, A.K., J. Organomet. Chem., 1982, vol. 224, p. 133.

    Article  Google Scholar 

  15. Kogure, K., Nakagawa, K., and Fukawa, H., Agric. Biol. Chem., 1976, vol. 40, p. 1547.

    Article  CAS  Google Scholar 

  16. Fu, C. and Ma, S., Org. Lett., 2005, vol. 7, p. 1707.

    Article  CAS  Google Scholar 

  17. Fidelibus, P.M., Gerbino, D.C., Mandolesi, S.D., and Podesta, J.C., Arkivoc, 2007, part (iv), p. 389.

    Google Scholar 

  18. Baird, M.S. and Hussain, H.H., Tetrahedron, 1987, vol. 43, p. 215.

    Article  CAS  Google Scholar 

  19. Pomerantz, F. and Fink, R., J. Labelled Compd. Radiopharm., 1979, vol. 16, p. 275.

    Article  CAS  Google Scholar 

  20. D’yakonov, I.A., Razin, V.V., and Komendantov, M.I., Tetrahedron Lett., 1966, vol. 7, p. 1135.

    Article  Google Scholar 

  21. D’yakonov, I.A., Razin, V.V., and Komendantov, M.I., Zh. Org. Khim., 1972, vol. 8, p. 54.

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    V. V. Razin & M. E. Yakovlev

  2. Ogarev Mordovia State University, Bol’shevistskaya ul. 68, Saransk, 430005, Republic of Mordovia, Russia

    V. A. Vasin

Authors
  1. V. V. Razin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. E. Yakovlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Vasin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © V.V. Razin, M.E. Yakovlev, V.A. Vasin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 7, pp. 990–994.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Razin, V.V., Yakovlev, M.E. & Vasin, V.A. Thermal decomposition products of methyl 1,5-diphenyl- and 5-methyl-1-phenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-exo-carboxylates. Russ J Org Chem 49, 974–978 (2013). https://doi.org/10.1134/S1070428013070038

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013070038

Keywords

Search

Navigation