13C-NMR. Spectra, Structure and Reactivity of Cyclic Oxocarbons
| Autor: | Wolfgang von Philipsborn, Roger Hollenstein, Werner Städeli |
|---|---|
| Rok vydání: | 1977 |
| Předmět: |
Rhodizonic acid
Decarboxylation Croconic acid Organic Chemistry Decahydroxycyclopentane Squaric acid Photochemistry Biochemistry Medicinal chemistry Redox Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Drug Discovery Reactivity (chemistry) Physical and Theoretical Chemistry Tetrahydrofuran |
| Zdroj: | Helvetica Chimica Acta. 60:948-958 |
| ISSN: | 0018-019X |
| DOI: | 10.1002/hlca.19770600325 |
| Popis: | The structures of cyclic polyketones, their hydrates and reduction products were studied in different solvents by 13C-NMR. spectroscopy. In dimethylsulfoxide solution rhodizonic acid (1), croconic acid (2) and squaric acid (3) exhibit signal averaging. In anhydrous tetrahydrofuran 1 and 2 could be observed as non-dynamic species. The spontaneous reactions of dodecahydroxycyclohexane (5) and decahydroxycyclopentane (‘leuconic acid’) (6) and the sequence of formation of ring-contracted products were investigated. Key intermediates could be clearly identified which support the mechanism proposed earlier involving a benzylic acid type rearrangement followed by decarboxylation and subsequent redox reactions. |
| Databáze: | OpenAIRE |
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