Reactions of boranes with carbonyl compounds: an investigation

The reaction of trialkylboranes with carbonyl reagents has not yet been reported. Trialkylboranes are nonnucleophilic, and thus do not participate in reactions with typical organic electrophiles. Modifications of the Lewis acidity of the borane are reported. Polarization of the carbonyl moiety was also investigated. Solvents, Lewis acids, and several carbonyl derivatives were investigated for their ability to polarize the carbonyl group.