Abstract
cis,cis-Cyclohexane-1,3,5-tricarboxylic acid (1) its trimethyl ester (2) and their 1,3,5-trimethylated and 1,3,5-tribenzylated derivatives were prepared, and their structures studied by two-dimensional NMR spectroscopy in conjunction with X-ray crystallography. The results show that these molecules adopt a chair conformation in solution, with all the carboxyl groups in1 and all the methoxycarbonyl groups in2 occupying the equatorial positions, but with the corresponding functionalities in the alkylated derivatives occupying the axial positions. For2, its 1,3,5-tribenzylated derivative4, andcis,cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid (5), the same conformational preferences are seen to persist in the crystalline state as in solution.
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References
Boundjouk, P., Kapfer, C. A., and Cunico, R. F. (1983)Organometallics 2, 336–343.
Chan, T.-L., Cui, Y.-X., Mak, T. C. W., Wang, R.-J., and Wong, H. N. C. (1990)Acta Crystallogr. A 46, Supplement, C191.
Diamond, R. (1969)Acta Crystallogr. A 25, 43–55.
International Tables for X-ray Crystallography (1974) Vol. IV (Kynoch Press, Birmingham, England), pp. 55, 99, 149. (Now distributed by Kluwer Academic Publisher, Dordrecht.)
Kemp, D. S., and Petrakis, K. S. (1981)J. Org. Chem. 46, 5140–5143.
Kopfmann, G., and Huber, R. (1968)Acta Crystallogr. A 24, 348–351.
Lindsey, L. S., Kearney, P. C., Duff, R. J. Tjivikua, P. T., and Rebek, J. (1988)J. Am. Chem. Soc. 110, 6575–6577.
Marshall, L., Parris, K., and Rebek, J. (1988)J. Am. Chem. Soc. 110, 5192–5193.
Menger, F. M., Chicklo, P. A., and Sherrod, M. J. (1989)Tetrahedron Lett. 30, 6943–6946.
Rebek, J. (1989)Pure Appl. Chem. 61, 1517–1522.
Rebek, J., Askew, B., Ballester, P., and Doa, M. (1987a)J. Am. Chem. Soc. 109, 4119–4120.
Rebek, J., Askew, B., Killoran, M., Nemeth, D., and Lin, F.-T. (1987b)J. Am. Chem. Soc. 109, 2426–2431.
Rebek, J., Marshall, L., Wolak, R., Parris, K., Killoran, M., Askew, B., Nemeth, D., and Islam, N. (1985)J. Am. Chem. Soc. 107, 7476–7481.
Sheldrick, G. M. (1985) inCrystallographic Computing 3: Data Collection, Structure Determination, Proteins and Databases, G. M. Sheldrick, C. Krüger, and R. Goddard (eds.) Oxford University Press, New York), pp. 175–189.
Steitz, A., Jr. (1968)J. Org. Chem. 23, 2978–2979.
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On leave from The National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China.
On leave from Central Laboratory, Nankai University, Tianjin, China.
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Chan, TL., Cui, YX., Mak, T.C.W. et al. Structural studies of some derivatives of cis, cis-cyclohexane-1,3,5-tricarboxylic acid. Journal of Crystallographic and Spectroscopic Research 21, 297–308 (1991). https://doi.org/10.1007/BF01156081
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DOI: https://doi.org/10.1007/BF01156081