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Theoretical discussion of cyclodimerization of nitrile N-oxides to furoxans

  • V. É. Turs
  • N. M. Lyapin
  • V. A. Shlyapochnikov
Brief Communications

Conclusions

  1. 1.

    Based on the data of quantum-chemical calculations the cyclodimerization of nitrile N-oxides is a two-step reaction with the formation of cis-dinitrosoethylene as an intermediate product, whose structure is determined by the stereospecificity of the reaction.

     
  2. 2.

    In the first transition state two molecules of the nitrile N-oxides are found in perpendicular planes, forming a molecular system with a C2 symmetry, whose structure is determined by the regioselectivity of the reaction.

     

Keywords

Transition State Nitrile Intermediate Product Molecular System Theoretical Discussion 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, West Berlin-Heidelberg (1971), Chapter 4.Google Scholar
  2. 2.
    W. R. Mitchell and R. M. Paton, Tetrahedron Lett.,1979, 2443.Google Scholar
  3. 3.
    F. B. Mallory and A. Cammarata, J. Am. Chem. Soc.,88, 61 (1966).Google Scholar
  4. 4.
    I. Yavari, R. E. Botto, and J. D. Roberts, J. Org. Chem.,43, 2542 (1978).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • V. É. Turs
    • 1
  • N. M. Lyapin
    • 1
  • V. A. Shlyapochnikov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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