The spatial structure of the isomeric dimethyl esters of 4-hydroxypiperidine-2, 6-dicarboxylic acid
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Three isomeric dimethyl esters of 4-hydroxypiperidine-2, 6-dicarboxylic acid have been isolated. The spatial structures of all three isomeric esters and of the acids corresponding to them have been established on the basis of NMR spectra. It has been shown that while the isomers I and II exist in the form of only one conformation each, isomer III in neutral and acid media apparently consists of an equilibrium mixture of two (or more) conformers. The information obtained on the spatial structure of the isomeric esters shows that the cyclization of these compounds with benzylamine and p-nitrobenzaldehyde takes place with the inversion of the piperidine ring.
KeywordsEster Organic Chemistry Dimethyl Spatial Structure Acid Medium
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- 1.E. S. Nikitskaya, V. S. Usovskaya, E. I. Levkoeva, and M. V. Rubtsov, USSR patent no. 164047; Byull. izobr., no. 14, 20, 1964.Google Scholar
- 2.E. S. Nikitskaya, E. I. Levkoeva, V. S. Usovskaya, and M. V. Rubtsov, KhGS [Chemistry of Heterocyclic Compounds], 296, 1965.Google Scholar
- 3.E. S. Nikitskaya, E. I. Levkoeva, V. S. Usovskaya, and M. V. Rubtsov, ZhOrKh, 1, 175, 1965.Google Scholar
- 4.G. Fodor and K. Nador, J. Chem. Soc., 721, 1953.Google Scholar
- 5.M. Balasubramanian, N. Padma, Tetrah. Lett., 49, 1963.Google Scholar
- 6.R. E. Lyle, J. Org. Chem., 22, 1280, 1957.Google Scholar
- 7.C.-Y. Chen and R. J. W. Le Fevre, J. Chem. Soc., 3467, 1965.Google Scholar
- 8.N. Bhacca and D. Williams, Applications of NMR Spectroscopy in Organic Chemistry, illustrations from the Steroid Field [Russian translation], Mir, Moscow, 66, 1966.Google Scholar