Abstract
The MINDO3, MNDO, AM1, and PM3 methods have been used to optimize the geometries of (+)-(4S,5S)-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane and (+)-(4S,5S)-4-phenyl-1-aza-3,7-dioxabicyclo-[3.3.0]octane. It has been shown that the stereospecificity, of the reaction of the former with methyl iodide is due to the high stability of one of the possible conformers.
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References
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Pharmacy Faculty 28, University of the Auvergne, Henri Dunant Place, Clermont-Ferrand, France; Samara State University, Samara 443011, Russia; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1424–1427, October, 1999.
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Couquelet, J., Madesclaire, M., Leal, F. et al. Stereospecificity of the reaction of (+)-(4S, 5S)-4-(4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane with methyl iodide. Chem Heterocycl Compd 35, 1242–1244 (1999). https://doi.org/10.1007/BF02323386
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DOI: https://doi.org/10.1007/BF02323386