Skip to main content
SpringerLink
Log in

Wolff rearrangement of alkoxycarbonylcarbenes during thermal decomposition of alkyl diazoacetates in presence of gaseous unsaturated compounds

  • Brief Communications
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The Wolff rearrangement of alkoxycarbonylcarbenes under the conditions for the thermal decomposition of alkyl diazoacetates was discovered for the first time. We also determined the conditions for the cycloaddition of the thus formed alkoxyketenes to alkenes, dimethylacetylene, and butadiene to give the previously unknown alkoxycyclobutanones and alkoxycyclobutenones.

  2. 2.

    The thermal isomerization of vinylalkoxycyclobutanones to alkoxycyclohexenones was discovered.

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

Literature cited

  1. I. E. Dolgii, E. A, Shapiro, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 1676.

  2. E. A. Shapiro and I. E. Dolgii, Second All-Union Convention on the Chemistry of Carbenes and Their Analogs, Abstracts of Papers [in Russian], Nauka (1977), p. 62.

  3. T. DoMinh and O. P. Strausz, J. Am. Chem. Soc.,92, 1768 (1970).

    Google Scholar 

  4. D. E. Thornton, R. K. Gosavi, and O. P. Strausz, J. Am. Chem. Soc.,92, 1768 (1970).

    Google Scholar 

  5. D. C. Richardson, M. E. Hendrick, and M. Jones, Jr., J. Am. Chem. Soc.,93, 3790 (1971).

    Google Scholar 

  6. R. J. Ellis and H. M. Frey, Trans. Faraday Soc.,59, 2076 (1963).

    Google Scholar 

  7. C. G. Overberger and A. E. Borchert, J. Am. Chem. Soc.,82, 1007 (1960).

    Google Scholar 

  8. M. Bertrand, G. Gil, A. Junino, and R. Maurin, Tetrahedron Lett.,1977, 1779.

  9. I. E. Dolgii, E. A. Shapiro, A. Ya. Shteinshneider, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim.,1977, 2514.

  10. R. Shriner et al., Systematic Identification of Organic Compounds, Wiley (1964).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    O. M. Nefedov, I. E. Dolgii & E. A. Shapiro

Authors
  1. O. M. Nefedov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. E. Dolgii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Shapiro
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for preliminary communications; a part of the work was presented at the Second All-Union Convention on the Chemistry of Carbenes and Their Analogs [2].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1209–1213, May, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nefedov, O.M., Dolgii, I.E. & Shapiro, E.A. Wolff rearrangement of alkoxycarbonylcarbenes during thermal decomposition of alkyl diazoacetates in presence of gaseous unsaturated compounds. Russ Chem Bull 27, 1052–1055 (1978). https://doi.org/10.1007/BF00929032

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00929032

Keywords

Search

Navigation