Photooxygenation of the CN bond: a mild new method for oxidative CC cleavage
✍ Scribed by Nüket Öcal; Lovelle M. Yano; Ihsan Erden
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 132 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
📜 SIMILAR VOLUMES
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 amidoxima
Mg(HSO 4 ) 2 in the presence of wet SiO 2 was reacted with oximes, hydrazones and semicarbazones and converts them to the corresponding carbonyl compounds in good to high yields under mild and heterogeneous conditions.