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The outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions.

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.

SUBMITTER: Ahamed M 

PROVIDER: S-EPMC3477162 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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The outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions.

Ahamed Muneer M   Ahamed Muneer M   Chan Bun B   Jensen Paul P   Todd Matthew H MH  

PloS one 20121019 10

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. ...[more]