Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis

• Published in: Monatshefte für Chemie Vol. 150; no. 2; pp. 353 - 362
• Main Authors: Kazemi, Foad, Ramdar, Moosa, Davarpanah, Jamal
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01-02-2019; Springer Nature B.V
• Subjects: Aldehydes; Aliphatic compounds; Analytical Chemistry; Catalysis; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Condensates; Inorganic Chemistry; Nitro compounds; Organic Chemistry; Original Paper; Oximes; Physical Chemistry; Reduction; Sodium carbonate; Tetrahydrofuran; Theoretical and Computational Chemistry; Oxime; Aliphatic nitro; Dinitrone; Nitrone; Nitrone–oxime
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-018-2326-4

Reduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux and at 55 °C conditions, respectively, in tetrahydrofuran using SnCl
2
·2H
2
O and Na
2
CO
3
. It was found that the presence of a catalytic amount of carboxylic acid such as 3-phenylpropanoic acid increases the yield of dinitrones versus nitrone–oxime and dioxime when dialdehydes were used as aldehyde source.
Graphical abstract