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- Title
Tautomeric and conformational equilibria of γ-lactones derived from (3,5-dibromo-1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid.
- Authors
Santalova, E.; Glazunov, V.; Denisenko, V.
- Abstract
Tautomeric transformation of (3,5-dibromo-1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid into previously unknown stereoisomeric γ-lactones, (3a S*,7 S*,7a R*)- and (3a S*,7 R*,7a R*)-5,7-dibromo-3ahydroxy-3,3a,7,7a-tetrahydro-1-benzofuran-2,6-diones, was revealed by H NMR spectroscopy. The concentration of the acid tautomer increases as the solvent polarity rises. The ability of the cycloxexene ring in the lactones to undergo inversion in solution is determined by orientation of the bromine atom on C.
- Subjects
ACETIC acid; CELL polarity; SPECTRUM analysis; LACTONES; ETHYLENE dibromide; CYCLOHEXANONES
- Publication
Russian Journal of Organic Chemistry, 2011, Vol 47, Issue 10, p1487
- ISSN
1070-4280
- Publication type
Academic Journal
- DOI
10.1134/S1070428011100058