Conclusions
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1.
We accomplished the preparative separation of a number of stereoisomeric 1,3-dioxolanes by the circulatory GLC method with an efficiency greater than 30 thousand theoretical plates.
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2.
Using the PMR spectra of 2-substituted 4,5-diisopropyl-1,3-dioxolanes, we identified the isomers on the basis of differences in the chemical shifts of the signals from the proton and substituent in the 2 position in cis-syn and cis-anti isomers.
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3.
We determined the thermodynamic parameters of solution for the indicated stereoisomers. The given compounds have very small differences in the thermodynamic characteristics.
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Literature cited
M. Anteunis and F. Alderweireldt, Bull. Soc. Chim. Belg.,73, 889 (1964).
M. Anteunis and F. Alderweireldt, Bull. Soc. Chim. Belg.,73, 903 (1964).
M. Anteunis and F. Alderweireldt, Bull. Soc. Chim. Belg.,74, 488 (1965).
R. U. Lemieux, J. D. Stevens, and R. R. Fraser, Can. J. Chem.,40, 1955 (1962).
W. E. Willy, G. Binsch, and E. L. Eliel, J. Am. Chem. Soc.,92, 5394 (1970).
R. Böhm and E. Hannig, Pharmazie,26, 600 (1971).
Sa Le Thi Shuan and J. Wiemann, Bull. Soc. Chim. France, 4550 (1968).
Y. Rommelaere and M. Anteunis, Bull. Soc. Chim. Belg.,79, 11 (1970).
F. Kametani and Y. Sumi, Chem. and Pharm. Bull.,20, 1479 (1972).
M. P. Zabokritskii, B. A. Rudenko, and V. P. Chizhkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1627 (1977).
L. P. Kuhn, J. Am. Chem. Soc.,80, 5950 (1958).
M. P. Zabokritskii, B. A. Rudenko, and V. P. Chizhkov, in: Analytical and Preparative Application of Chromatography [in Russian], VNIITÉKhim., Moscow (1980), p. 62.
M. S. Vigdergauz and R. I. Izmailov, Application of Gas Chromatography for Determination of the Physicochemical Properties of Substances [in Russian], Nauka, Moscow (1970).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2277–2281, October, 1982.
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Zabokritskii, M.P., Bukin, V.A. & Rudenko, B.A. Gas chromatographic separation of some stereoisomeric dioxolanes and their identification using PMR spectroscopy. Russ Chem Bull 31, 2005–2008 (1982). https://doi.org/10.1007/BF00950642
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DOI: https://doi.org/10.1007/BF00950642