The
reaction between (F3C)2BNMe2, 1, 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. Instead, a mechanism in which the
ene reaction product is attacked by a second molecule of 1, followed by hydrogen transfer and decomposition, exhibits barriers
lower than that for the ene reaction. The mechanism implies that the
fragment of 1 in the observed product is not the one
that underwent the ene reaction. The ene reaction barrier is rate-determining,
and it is low enough to conform to the experimental conditions.