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2-Methyl-5-hexyl- and 2-isopropyl-5-hexyl-1, 3-dioxanes have been synthesized for the first time by the condensation of 2-hexyl-1, 3-propane-diol with acetaldehyde and isobutyraldehyde, and they have been separated into their stereoisomers by fractionation in efficient columns. It has been shown by a study of their PMR spectra that the low-boiling isomers have the cis- and the high-boiling isomers the trans-configuration. A study of the PMR spectra has enabled us to show not only the configuration but also the predominant conformations of the isomers; the cis-isomer exists predominantly in the unsymmetrical boat conformation with a diequatorial location of the substituents and the trans-isomer in the chair conformation, also with a diequatorial arrangement of the substituents.
KeywordsAcetaldehyde Organic Chemistry Fractionation Chair Conformation Efficient Column
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- 1.A. V. Bogatskii, Yu. Yu. Samitov, N. L. Garkovik, and S. A. Andronati, KhGS [Chemistry of Heterocyclic Compounds], 2, 674, 1966.Google Scholar
- 2.A. V. Bogatskii and N. L. Garkovik, ZhOKh, collection 2, p. 42, 1965.Google Scholar
- 3.C. Barbier, I. Delman, and T. Ranft, Tetrah. Let., 3339, 1964.Google Scholar
- 4.J. Delman and C. Barbier, J. Chem. Phys., 41, 1106, 1964.Google Scholar
- 5.H. Conroy, Adum. Org. Chem., [Russian translation], 265, 1960.Google Scholar
- 6.H. Gutowski, M. Karplus, and D. Granti, J. Chem. Phys., 31, 1278, 1959.Google Scholar
- 7.A. V. Bogatskii, Yu. Yu. Samitov, and N. L. Garkovik, ZhOrKh, 2, 1335, 1966.Google Scholar
- 8.M. Conrad and C. Bischoff, Ann., 204, 143, 1880.Google Scholar
- 9.E. Wiberg and M. Schmidt, Z. Naturforsch, 76-b, 59, 1952.Google Scholar
- 10.Z. D. Bogatskaya, Ti Fu-pao, V. E. Ivashchenko, and A. F. Galatin, ZhOKh, 32, 2282, 1962.Google Scholar