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Oxidative cleavage of the CN bond during singlet oxygenations of amidoximates

✍ Scribed by Nüket Öcal; Ihsan Erden

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
92 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Amidoximes are inert toward singlet oxygen ( 1 O 2 ), however, the photooxygenation of amidoximate anions proceeds smoothly and in high yield to give mixtures of amides and nitriles. The mechanism of these reactions appears to involve carbonyl oxide intermediates. The oxidative cleavage of amidoximates closely resembles the results obtained from nitric oxide synthase (NOS) oxidations of N-hydroxyarginine.

📜 SIMILAR VOLUMES

Photooxygenation of the CN bond: a mild
Photooxygenation of the CN bond: a mild new method for oxidative CC cleavage
✍ Nüket Öcal; Lovelle M. Yano; Ihsan Erden 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 132 KB

Upon photooxygenation in the presence of base, a-oximinocarbonyl compounds undergo clean oxidative C C cleavage giving rise to mixtures of esters and acids. The mechanism of these reactions involves some unusual peroxidic intermediates, including a 2,3,5-trioxapentanes.