Computational Study of the Ene/Rearrangement Reaction between (FC)B═NMe, , and Acetonitrile: Reactant-Catalyzed Mechanism of the Ketenimine-Nitrile-Like Rearrangement.

The reaction between (FC)B═NMe, , and acetonitrile at low temperature in pentane yields a bora-acetonitrile rather than the expected coordination complex. This appears to arise from the two undergoing an ene reaction followed by a rearrangement analogous to a ketenimine-nitrile rearrangement. Computational studies indicate that mechanistic steps suggested for the latter require energies too large for the reaction to take place under the experimental conditions.