Publication details

Glycoluril Dimer Isomerization under Aqueous Acidic Conditions

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Authors

ŠTANCL Marek GARGULÁKOVÁ Zuzana ŠINDELÁŘ Vladimír

Year of publication 2012
Type Article in Periodical
Magazine / Source The Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
web http://pubs.acs.org/doi/abs/10.1021/jo302063j
Doi http://dx.doi.org/10.1021/jo302063j
Field Organic chemistry
Keywords cucurbiturils; glycolurils; isomerization; dimers
Description A water-soluble methylene-bridged glycoluril dimer 2S was isolated. It was shown that 2S is the only kinetic product of the reaction between glycoluril derivative 1 and paraformaldehyde. Compound 2S is subsequently intermolecularly transformed into its diastereomer 2C. The kinetics and thermodynamics of the S- to C-shaped dimer isomerization were investigated under reaction conditions similar to those for cucurbituril synthesis.
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