Solvent-free condensation of phenylacetonitrile and nonanenitrile with 4-methoxybenzaldehyde: optimization and mechanistic studies.
The condensation of phenylacetonitrile with 4-methoxybenzaldehyde can be carried out by two solvent-free methods: i) using neat powdered KOH at room temperature with equivalent amounts of aldehyde, nitrile and base for 3 min, and ii) using K2CO3 in the presence of a phase transfer agent for 3 min under microwave activation or conventional heating. By extending the reaction time up to 10 min, four different products were obtained from phenyl or nitrile group migration. With nonanenitrile, only the second method could be applied to give two kinds of condensed compounds with or without phenyl (or nitrile) group migration. The intervention of non-thermal MW-specific effects was proved in some cases and interpreted.
Loupy
André
A
Laboratoire des Réactions Sélectives sur Supports, ICMMO, CNRS UMR 8615, Université Paris-Sud, Orsay, France.
Pellet
Michèle
M
Petit
Alain
A
Vo-Thanh
Giang
G
D000097:Acetonitriles / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D002849:Chromatography, Gas; D006358:Hot Temperature; D015394:Molecular Structure; D008970:Molecular Weight; D009570:Nitriles / Q000737:chemistry*; D012997:Solvents
D000097:Acetonitriles; D001547:Benzaldehydes; D009570:Nitriles; D012997:Solvents; C006725:benzyl cyanide; C511167:nonanenitrile; C024896:4-anisaldehyde