Journal of Structural Chemistry p. 908 - 914 (1997)
Update date:2022-08-16
Topics:
Melnitskaya
Kuramshin
Khlebnikova
Melnitskii
Kantor
Quantum chemical calculations and the PMR method are used to show that the preferable conformation of cyclic furfural acetals is a chair with an axial orientation of the furyl substituent. In 2-(furyl-2′)-5-ethyl-5-oxymethyl-1,3-dioxane, the conformation equilibrium is shifted toward the trans-isomer with diaxial positions of the furyl and oxymethyl groups. The results of calculations suggest that the synthesis can lead to a cis-isomer with an axial orientation of the furyl and equatorial oxymethyl groups. It was shown experimentally that the synthesis leads to a mixture of trans- and cis-isomers. Mild conditions (room temperature, aqueous medium) lead to formation of the trans-isomer and small amounts of the cis-isomer (less than 2%). In rigid conditions (boiling in aromatic hydrocarbons), up to 20% of the cis-isomer is formed. 1998 Plenum Publishing Corporation.
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