Abstract
The Oxidation of Two New 1,3-Dihydroxyimidazolidines – Synthesis and Structure of Nitronyl Nitroxide Radicals The two new 1,3-dihydroxyimidazolidines 3a and 3b were prepared by condensation of 4-formylbenzoic acid (2a) and sodium glyoxylate (2b) with 2,3-dimethyl-2,3-butanediylbis-(hydroxylamine) sulfate (1). The 1,3-dihydroxyimidazolidines were oxidized with sodium periodate in water to form nitronyl nitroxide radicals. Oxidation of the 1,3-dihydroxyimidazolidine 3a yielded the new radical 4a, whereas the product obtained from the 1,3-dihydroxyimidazolidine 3b was, due to decarboxylation, the unsubstituted radical 4c. The crystal structure of 4a was solved by single-crystal X-ray diffraction, showing the molecules to be arranged in zigzag chains as a consequence of intermolecular hydrogen bonds.
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