Abstract
In the reaction of the cis-syn-cis and cis-anti-cis diastereomers of dicyclohexano-18-crown-6 with 2-nitro and 2,4-dinitroaniline crystalline complexes with a 1:2 stoichiometric composition were obtained only when the cis-anti-cis diastereomer was used. The three-dimensional structure of the complex of the cis-anti-cis diastereomer of dicyclohexano-18-crown-6 with 2,4-dinitroaniline was determined by an x-ray diffraction study. The complexing of o-nitroanilines with the cis-anti-cis diastereomer is explained by the topological conformity of the interacting compounds. The isolation of the individual cis diastereomers from the mixture of them formed as a result of the catalytic hydrogenation of dibenzo-18-crown-6 was accomplished by means of the selective formation of the crystalline complex of the cis-anti-cis diastereomer with 2-nitroaniline.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1190–1195, September, 1988.
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Ganin, é.V., Makarov, V.F., Kotlyar, S.A. et al. Synthesis and structures of molecular complexes of the cis-anti-cis diastereomer of dicyclohexano-18-crown-6 with o-nitroanilines. Chem Heterocycl Compd 24, 979–984 (1988). https://doi.org/10.1007/BF00474040
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DOI: https://doi.org/10.1007/BF00474040