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The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions
Journal article   Open access  Peer reviewed

The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions

Muneer Ahamed, Bun Chan, Paul Jensen and Matthew H. Todd
PloS one, Vol.7(10), pp.e47224-e47224
19/10/2012
DOI: https://doi.org/10.1371/journal.pone.0047224
PMCID: PMC3477162
PMID: 23094038

Abstract

Multidisciplinary Sciences Science & Technology Science & Technology - Other Topics
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.
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