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Aldehyde-enamines from α-oxocarboxylic acids. A facile and general route to aldehydes via decarboxylation of α-oxocarboxylic acids carrying β-hydrogens

✍ Scribed by Ioannis K. Stamos

Book ID
104220360
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
213 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

When a-oxocarboxylic acids carrying 8-hydrogens are treated with a secondary amine in boiling benzene with azeotropic removal of water, they decarboxylate quantitatively to form aldehyde-enamines which subsequently are hydrolyzed to the corresponding aldehydes in high yields. a-Oxocarboxylic acids are compounds of biological importance and their decarboxylation is a significant biological process'. Chemically such decarboxylations at least for the more reactive acids such as mesoxalic, glyoxalic, oxaloacedic, pyruvic and dioxogulonic, are promoted by metal ions and/or primary amines2.

📜 SIMILAR VOLUMES

Addition of alkyl radicals, generated fr
Addition of alkyl radicals, generated from carboxylic acids via photochemical decarboxylation, to glyoxylic oxime ether: a mild and efficient route to α-substituted α-aminoesters
✍ Yasuharu Yoshimi; Kosuke Kobayashi; Hayato Kamakura; Keisuke Nishikawa; Yoshiki 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 505 KB

Radical addition to a glyoxylic oxime ether was accomplished under mild conditions using an alkyl radical generated from a free carboxylic acid via photochemical decarboxylation. The photoreaction provided an efficient route to a-substituted a-aminoesters from carboxylic acids and oxime ether.