Glycoluril Dimer Isomerization under Aqueous Acidic Conditions
| Authors | |
|---|---|
| Year of publication | 2012 |
| Type | Article in Periodical |
| Magazine / Source | The Journal of Organic Chemistry |
| MU Faculty or unit | |
| 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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