Abstract
The resolution of three chiral alcohols with O,O'-dibenzoyl-(2R,3R)-tartaric acid (DBTA) via diastereoisomeric supramolecular compound formation was investigated with thermoanalytical methods. On the basis of TG measurements the DBTA:chiral alcohol molar ratio in the compounds is 1:1 which agrees with the results of single-crystal X-ray diffraction analysis. The DBTA – chiral alcohol supramolecular compounds have different supramolecular structure than the DBTA – achiral alcohol supramolecular compounds. The supramolecular compounds containing cyclohexanols have higher thermal stability than the compounds containing acyclic aliphatic alcohols. The amount of unreacted DBTA monohydrate in the solid phase can be determined both with DSC and with TG measurements.
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REFERENCES
S. H. Wilen, Topics in Stereochem., 6 (1971) 107.
S. H. Wilen, Resolving Agents and Resolutions in Organic Chemistry, Notre Dame Univ. Press., Notre Dame, 1971.
E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, Inc., New York 1993, p. 153-295.
P. Newman, Optical Resolution Procedures for Chemical Compounds, Optical Resolution Information Center, Manhattan College, N.Y. Riverdale 1978–84.
L. Pasteur, Ann. Chim. et Phys., 24 (1848) 442.
D. Seebach, A. K. Beck, R. Imwinkelried, S. Roggo and A. Wonnacott, Helv. Chim. Acta, 70 (1987) 954.
E. Weber, C. Wimmer, A. L. Llamas-Saiz and C. Forces-Forces, J. Chem. Soc., Chem. Commun., (1992) 733.
M. C. Etter, Acc. Chem. Res., 23 (1990) 120.
F. Toda, K. Tanaka, L. Infantes, C. Foces-Foces, R. M. Claramunt and J. Elguero, J. Chem. Soc., Chem. Commun., (1995) 1453.
P. P. Korkas, E. Weber and G. Náray-Szabó, J. Chem. Soc., Chem. Commun., (1995) 2229.
S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 117 (1995) 7630.
K. Nemák, M. Ács, Zs. Jászay, D. Kozma and E. Fogassy, Tetrahedron, 52 (1996) 1637.
D. Kozma, Zs. Böcskei, Cs. Kassai, K. Simon and E. Fogassy, J. Chem. Soc. Chem. Comm., (1996) 753.
R. Illés et al., J. Therm. Anal. Cal., (in press).
Cs. Kassai et al., J. Am. Chem. Soc., (in press).
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Kassai, C., Illés, R., Pokol, G. et al. Thermoanalytical Study of O,O'-Dibenzoyl-(2R,3R)-Tartaric Acid Supramolecular Compounds Part II. Investigation of the resolution of racemic alcohols. Journal of Thermal Analysis and Calorimetry 62, 647–655 (2000). https://doi.org/10.1023/A:1012013106097
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DOI: https://doi.org/10.1023/A:1012013106097