Abstract
The problems of the structure—property interrelationship of 3-imino-2-oxabicyclo[2.2.1]heptane derivatives are discussed on the basis of x-ray diffraction studies (XDS). A pathway for the formation of the bicyclic compounds is proposed, and the realization of spirans in the reaction of sym-tetracyanoethane with conjugated cyclic systems containing s-cis C=C and C=O fragments is substantiated. The factors responsible for the syn orientation of the oxygen atom and the N-substituent of the imino group are analyzed. It is shown that a change in the steric hindrance in the bicyclic compounds leads to a change in the conformation of the latter. The reasons for the shortening of the Csp3-Csp3, Csp3-Csp and C=N exo bonds and the correlation of the XDS and IR spectroscopic data are examined. From the XDS data for N-bromo-substituted imines, a model for Br+...N≡C electrophilic attack was proposed
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Communication 16 from the series “Chemistry of 1,1,2,2-tetracyanoethane”. See [1] for Communication 15.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 519–526, April, 1991.
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Zolotoi, A.B., Lukin, P.M., Konovalikhin, S.V. et al. Formation pathways and structure—Property interrelationship of 3-imino-1-methyl-5,5-dialkyl-4,7,7-tricyano-2-oxabicyclo-[2.2.1]heptane derivatives. Chem Heterocycl Compd 27, 413–419 (1991). https://doi.org/10.1007/BF00480841
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DOI: https://doi.org/10.1007/BF00480841