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13C-NMR. Spectra, Structure and Reactivity of Cyclic Oxocarbons

✍ Scribed by Werner Städeli; Roger Hollenstein; Wolfgang Von Philipsborn

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
565 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The structures of cyclic polyketones, their hydrates and reduction products were studied in different solvents by ^13^C‐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.

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