The Preparation of Di-n-butylboron Cyanide by the Interaction of Di-n-butylboron Chloride with Trimethylsilyl Cyanide¹

Abstract

melting points and other physical properties of the compounds would lead one to expect.In conclusion, it appears that these trimers are both in the chair form with nearly coplanar arrangements of the valence bonds of the nitrogen atoms. The latter feature is not surprising, to judge from the dipole moments and other properties of aromatic amines which yield values of the nitrogen valency angle. The attachment of a phenyl group to nitrogen seems to widen the valency angle of that atom. Such attachment apparently causes a change in the nitrogen bonding orbitals from sp3 to sp3 hybridization, with the lone pair of nitrogen electrons now in symmetric p-orbitals at right angles to the plane of the bonding orbitals. In this situation, the contribution of the lone pair to the molecular moment diminishes and the calculations made above are the more valid.Acknowledgments.-It is a great pleasure to acknowledge the friendly interest and advice given us by Drs. E. C. Wagner, . R. Nixon, F. V. Brutcher and R. E. Hughes. For aid in the preliminary stages of the experimentation we are also indebted to Messrs.

Catalytic carboborations

“…Cyanoboranes, however, had been rarely employed in organic synthesis. Dialkylcyanoborane and dihydrocyanoborane were prepared in the late 1950's, although their polymeric character hampered its use in organic synthesis 20. Alkoxy‐substituted cyanoboranes still have difficulty in handling, isolation, and utilization in organic synthesis.…”