Prout, Franklin S.; Beaucaire, Victor D.; Dyrkacz, Gary R.; Koppes, William M.; Kuznicki, Robert E.; Marlewski, Theordore A.; Pienkowski, James J.; Puda, Jacqueline M. published the article 《Knoevenagel Reaction. Kinetic study of the reaction of (+)-3-methyl-cyclohexanone with malononitrile》. Keywords: Knoevenagel condensation malononitrile methylcyclohexanone; cyclohexanone methyl malononitrile Knoevenagel condensation; amino acid catalyst Knoevenagel condensation.They researched the compound: cis-4-Aminocyclohexane carboxylic acid( cas:3685-23-2 ).Product Details of 3685-23-2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:3685-23-2) here.
The condensation of malononitrile with (+)-3-methylcyclohexanone produced an 80-85% yield of (-)-3-methylcyclohexylidenemalononitrile. The reaction, followed polarimetrically in aqueous alc., is kinetically second order and efficiently catalyzed by weak bases (ω-amino acids, cyclic amino acids, NH4OAc) furnishing solutions having an apparent pH 7.5-8.0. With β-alanine as catalyst, the Ea was 7.6 kcal/mole compared to 11 kcal/mole uncatalyzed. Stronger bases (Barbital, NaOAc, LOAc, KF, piperidine) effect more rapid condensation but poorer kinetics because of telomerization of malononitrile at the higher pHs.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate