Abstract
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.
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Bogatskii, A.V., Bogatskaya, Z.D., Samitov, Y.Y. et al. Six-membered heterocycles. Chem Heterocycl Compd 4, 444–447 (1971). https://doi.org/10.1007/BF00486752
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DOI: https://doi.org/10.1007/BF00486752