Abstract
The structure of diastereomeric methyl-7-anti-methoxy-7-syn-phenyl-and methyl-7-syn-methoxy-7-anti-phenyl-6-endo-bromobicyclo[3.1.1]heptane-6-exo-carboxylates 2a and 3a and their chlorine-and iodine-substituted analogs 2b and 3c was studied by XRD. The diastereomers differ in the geometrical parameters of the carbon framework of the molecules. The C(1)-C(2)-C(3)-C(4)-C(5)-C(6) six-membered ring is in the intermediate conformation between envelope and chair in structures 2 and envelope in structures 3. In compound 2a, the cyclobutane fragment has a higher degree of folding than in 3a; one of the possible reasons for that is the donor-acceptor interaction between the 6-methoxycarboxylic and 7-methoxy groups in molecule 2a.
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Original Russian Text Copyright © 2007 by V. V. Razin, Yu. A. Makarychev, V. A. Vasin, L. Hennig, and J. Baldamus
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Translated from Zhurnal Strukturnoi Khimii, Vol. 48, No. 6, pp. 1189–1196, November–December, 2007.
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Razin, V.V., Makarychev, Y.A., Vasin, V.A. et al. Structure of methyl-7-methoxy-7-phenyl-6-endo-halobicyclo[3.1.1]heptane-6-exo-carboxylate diastereomers in single crystals. J Struct Chem 48, 1124–1131 (2007). https://doi.org/10.1007/s10947-007-0180-z
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DOI: https://doi.org/10.1007/s10947-007-0180-z