The Outcome of the Oxidations of Unusual Enediamide Motifs Is Governed by the Stabilities of the Intermediate Iminium Ions |
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| Authors: | Muneer Ahamed Bun Chan Paul Jensen Matthew H. Todd |
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| Affiliation: | 1. School of Chemistry, The University of Sydney, Sydney, New South Wales, Australia.; 2. ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Victoria, Australia.; California Institute of Technology, United States of America, |
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| 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. |
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