Ring inversion in 5,5-disubstituted 1,3-dioxanes

Journal Article · Sat Oct 31 23:00:00 EST 1987 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)

DOI:https://doi.org/10.1007/BF00476374· OSTI ID:6961744

Bochkor, S A; Lapuka, L F; Kurmaeva, E S; Chalova, O B; Zlotskii, S S; Rakhmankulov, D L

The conformational mobility was studied by dynamic PMR and the free energies of activation of the conformational transitions of 5,5-bis(chloromethyl)-, 5,5-bis(iodomethyl)- and 2,3-pentamethylene-bis-5,5-bis(chloromethyl)-1,3-dioxanes were determined. The PMR spectra in toluene were studied over the temperature range of 20 to -70/sup 0/C. In the PMR spectra at room temperature, the resonance lines of the geminal protons of all the groups of the dioxane ring are in the form of fairly narrow singlets, which indicates a rapid chair-chair type inversion on the NMR time scale that is known for six-membered heterocycles. With decrease in temperature, the rate of the ring inversion decreases.

• Research Organization: Ufa Petroleum Institute (USSR)
• OSTI ID: 6961744
• Journal Information: Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 23:5; ISSN CHCCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTIVATION ENERGY
CHEMICAL REACTIONS
CHEMICAL SHIFT
CONFORMATIONAL CHANGES
ENERGY
HETEROCYCLIC COMPOUNDS
ISOMERIZATION
LINE BROADENING
LINE WIDTHS
NMR SPECTRA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
RELAXATION
SPECTRA
SPIN-SPIN RELAXATION
STEREOCHEMISTRY
TEMPERATURE DEPENDENCE