Reaction of 9-borabicyclo[3.3.1]nonane with N-trimethylsilylamines - Cleavage of the N-Si or N-H bond

Wrackmeyer B.; Kehr G.; Ali S.

Abstract

The reaction of dimeric 9-borabicyclo[3.3.1]nonane 1 with N-trimethylsilyl-aniline 2 affords 9-anilino-9-borabicyclo[3.3.1]nonane 5 by elimination of trimethylsilane. In contrast, 1 reacts with the N-trimethylsilyl-2-aminopyridines 3 and 4 selectively by elimination of H2 to give the corresponding N-trimethylsilyl-aminoboranes 6 and 7. The latter reactions proceed via formation of borane-pyridine adducts.