The Synthesis and Organic Chemistry of the Boron-Silicon Bond.
Final rept. 1 Oct 80-30 Sep 85,
PUERTO RICO UNIV RIO PIEDRAS
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The synthesis of the boron-silicon bond via the reaction of methyldiphenylsilyllithium with 9-borabicyclo 3.3.1 nonane and treatment of the hydridoborate complex with acid was accomplished. The B-silyl-9-BBN was difficult to separate and purify, but was nevertheless fully characterized. It showed very little reactivity, however. For example, it oxidized well with alkaline hydrogen peroxide and slowly in air, but was inert to methanol, water, bromine and tributyltin hydride. In addition it did not react with carbonyl compounds, nor with olefins or acetylenes under a variety of conditions. The reaction of silyllithium reagents with 9-BBN in the presence of N,N,N,N-tetramethylethylenediamine produced the corresponding borate in excellent yield as judged by 11B NMR analysis. These systems too were very unreactive, reacting well only with unhindered alcohols and very poorly with aldehydes and even acid chlorides. Attempts to prepare a stable, crystalline amine complex were unsuccessful.
- Organic Chemistry