68922-17-8Relevant articles and documents
Gem-diamines as highly active organocatalysts for carbon-carbon bond formation
Climent, Maria J.,Corma, Avelino,Dominguez, Irene,Iborra, Sara,Sabater, Maria J.,Sastre, German
, p. 136 - 146 (2007/10/03)
Diamines with neighbour nitrogen atoms have been used as base catalysts in the Knoevenagel condensation reaction between benzaldehyde and ethyl cyanoacetoacetate. The catalytic results show that a good basic catalyst requires a combination of two factors: high proton affinity and the ability to return the proton to the oxoanion intermediate. Computational chemistry calculations show this by characterizing the reactants, products, and transition states and by calculating the activation energies of the different reaction steps. A diamine, di(3-methylpiperidine)methane (B), has been found with a higher catalytic activity than DMAN despite its lower proton affinity, demonstrating that not only the proton affinity, but also the steric ability to abstract the protons, are important in explaining the catalytic results.
CONSECUTIVE MENSCHUTKIN REACTION OF CYCLIC AMINES WITH DICHLOROMETHANE UNDER HIGH PRESSURE: SYNTHESIS OF METHYLENEBISAMINES
Matsumoto, Kiyoshi,Hashimoto, Shiro,Ikemi, Yukio,Otani, Shinichi
, p. 1417 - 1420 (2007/10/02)
The reaction of heterocyclic amines such as pyrrolidine, piperidines, and morpholines with dichloromethane in methanol in the kilo bar region affording the corresponding methylenebisamines is described.
