Conclusions
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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.
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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.
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Literature cited
C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, West Berlin-Heidelberg (1971), Chapter 4.
W. R. Mitchell and R. M. Paton, Tetrahedron Lett.,1979, 2443.
F. B. Mallory and A. Cammarata, J. Am. Chem. Soc.,88, 61 (1966).
I. Yavari, R. E. Botto, and J. D. Roberts, J. Org. Chem.,43, 2542 (1978).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 214–216, January, 1982.
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Turs, V.É., Lyapin, N.M. & Shlyapochnikov, V.A. Theoretical discussion of cyclodimerization of nitrile N-oxides to furoxans. Russ Chem Bull 31, 202–204 (1982). https://doi.org/10.1007/BF00954445
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DOI: https://doi.org/10.1007/BF00954445