The outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions.
basic_science · Level V
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- Record sourced from PubMed, PMID 23094038.
- Also identified by DOI 10.1371/journal.pone.0047224 and PMC identifier PMC3176743.
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Abstract
We compare the results from the oxidation of two unusual "enediamide" motifs (3,4-dihydropyrazin-2(1H)-ones), where a double bond is flanked by two amides. In one case the oxidation led to a ring-opened product arising from the cleavage of the double bond, and in the other a rare cis-dioxygenated compound was obtained. Both products have been characterized by X-ray crystallography. The outcomes of the key reactions are rationalized based on calculated free energies of intermediates.