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

doi:10.1371/journal.pone.0047224

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 journal › Article › peer-review

2 Citations (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 language	English
Article number	e47224
Pages (from-to)	e47224
Number of pages	7
Journal	PLoS One
Volume	7
Issue number	10
DOIs	https://doi.org/10.1371/journal.pone.0047224
Publication status	Published - 19 Oct 2012

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

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