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

Tautomeric and conformational equilibria of γ-lactones derived from (3,5-dibromo-1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetic acid.

Santalova, E.; Glazunov, V.; Denisenko, V.