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, Matthew Todd

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    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.

    Original languageEnglish
    Article numbere47224
    Pages (from-to)e47224
    Number of pages7
    JournalPLoS One
    Volume7
    Issue number10
    DOIs
    Publication statusPublished - 19 Oct 2012

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