Conclusions
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1.
The reaction of the isomeric 2,3-dichlorotetrahydropyrans with Grignard reagents obeys thermodynamic control; the formed 2-R-3-Cl-tetrahydropyrans have the conformation of an armchair with a diequatorial arrangement of the substituents.
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2.
2,3-Di-(p-chlorophenyl)-1,4-dioxane, obtained from 2,3-dichloro-1,4-dioxane and p-ClC6H4MgBr, is found in the conformation of an armchair with a cis-orientation of the phenyl rings.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 377–381, February, 1974.
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Arbuzov, B.A., Klimovitskii, E.N., Yuldasheva, L.K. et al. Stereochemistry of reaction of 2,3-dichlorotetrahydropyrans with Grignard reagents. Russ Chem Bull 23, 343–346 (1974). https://doi.org/10.1007/BF00924684
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DOI: https://doi.org/10.1007/BF00924684