Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr<sub>4</sub>‐Catalyzed Schiff Condensation
Sevilya N. Yunusova, Dmitrii S. Bolotin, Mikhail A. Vovk, Peter M. Tolstoy, Vadim Yu. Kukushkin
Abstract
Tetrabromomethane functions as an organic catalyst for non‐redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N ‐acyl hydrazones. This simple, inexpensive, and commercially available halomethane provides up to 14‐fold acceleration of the Schiff reaction; the kinetic data indicate that the studied condensation exhibits the first order on CBr 4 . The catalytic activity of CBr 4 is significantly higher than the activity of other halogen‐containing species, such as CHX 3 or ArX (X = Cl, Br, I).
Topics & Concepts
ChemistryCatalysisAldehydeHydrazideCondensation reactionCondensationKinetic energyRedoxOrganic chemistryQuantum mechanicsThermodynamicsPhysicsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryChemical Reaction MechanismsCatalytic Cross-Coupling Reactions