Theoretical discussion of cyclodimerization of nitrile N-oxides to furoxans
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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.
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.
KeywordsTransition State Nitrile Intermediate Product Molecular System Theoretical Discussion
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- 1.C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, West Berlin-Heidelberg (1971), Chapter 4.Google Scholar
- 2.W. R. Mitchell and R. M. Paton, Tetrahedron Lett.,1979, 2443.Google Scholar
- 3.F. B. Mallory and A. Cammarata, J. Am. Chem. Soc.,88, 61 (1966).Google Scholar
- 4.I. Yavari, R. E. Botto, and J. D. Roberts, J. Org. Chem.,43, 2542 (1978).Google Scholar