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Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N-hydroxyphthalimide and Co salts

✍ Scribed by Francesco Minisci; Francesco Recupero; Andrea Cecchetto; Carlo Punta; Cristian Gambarotti; Francesca Fontana; Gian Franco Pedulli

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
41 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N‐oxyl radical (PINO) generated from N‐hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearo‐matised in a chain process. Quinazoline has an anomalous behaviour, giving 3__H__‐quinazolin‐4‐one as the only reaction product.

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A new selective free radical synthesis o
A new selective free radical synthesis of aromatic aldehydes by aerobic oxidation of tertiary benzylamines catalysed by N-hydroxyimides and Co(II) under mild conditions. Polar and enthalpic effects
✍ Andrea Cecchetto; Francesco Minisci; Francesco Recupero; Francesca Fontana; Gian 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 107 KB

Tertiary benzylamides are easily and selectively converted into aldehydes by molecular oxygen; the reaction is catalysed by N-hydroxyamides and Co(II).