Abstract
Phenyldimethylsilyllithium reacts with nitriles by several substantially different pathways depending upon the structure of the nitrile. The products include the acylsilane 2 from pivalonitrile ( 1), cumylsilane 5 from 2-phenylisobutyronitrile ( 4), the α-anion from phenylacetonitrile ( 9), and a mixture of benzil ( 15) and 2,4,5-triphenylimidazole ( 17) from benzonitrile ( 13).
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