Tetrahedron p. 1167 - 1179 (1983)
Update date:2022-07-30
Topics:
Guyot, J.
Kergomard, A.
The kinetics of the reaction of (+)-3-methyl cyclohexanone with malonitrile were studied in benzene at 25 deg C, in the presence of hexylamine-acetic acid mixtures.Hexylamine gives an imine with cyclohexanone in an acid-catalyzed step.This imine then reacts quickly with malononitrile.A rate law of zero order in malononitrile is observed.Separate kinetic results obtained for the formation of the imine and for the imine-malonitrile reaction support this mechanism.Without acetic acid, a complex rate law is observed; hexylamine acts mainly as a basic catalyst.Primary amine-carboxylic acid was used as a catalyst in Knoevenagel reaction, often giving an increase in yield and a diminution in the reaction time compared with the more commonly used catalysts: piperidine, β-alanine, AcOH-AcONH4.
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Doi:10.1016/S0040-4039(00)81514-2
(1983)Doi:10.1055/s-1983-30330
(1983)Doi:10.1007/s10593-007-0032-y
(2007)Doi:10.1016/j.saa.2004.08.028
()Doi:10.1021/jo050994h
(2005)Doi:10.1021/ja00292a017
(1985)
