The outcome of the oxidations of unusual enediamide motifs is governed by the stabilities of the intermediate iminium ions.
oleh: Muneer Ahamed, Muneer Ahamed, Bun Chan, Paul Jensen, Matthew H Todd
| Format: | Article |
|---|---|
| Diterbitkan: | Public Library of Science (PLoS) 2012-01-01 |
Deskripsi
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.