V. V. Gavrilov, M. Shamsutdinov, G. A. Chmutova
Dec 1, 2007
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Journal
Russian Journal of Organic Chemistry
Abstract
Spiro[cyclohexane-1,4′-[3,5]dioxabicyclo[5.1.0]octanes] were synthesized, and their conformational behavior was studied by dynamic 13C NMR spectroscopy. Anancomeric displacement of conformational equilibrium toward two nonequivalent twist conformers with close energies was revealed. The relative Gibbs energies ΔGo and enthalpies of formation ΔHo of twist and chair-like conformers with endo and exo orientation of the three-membered ring of structurally related formaldehyde and acetone acetals were calculated in terms of the density functional theory at the B3LYP/6-31G(d,p) level. Like spiro-cyclohexane analogs, they were shown to have a non-chair conformation.