Magnesium Boryl Reactivity with 9-BBN and Ph3 B: Rational B-B' Bond Formation and Diborane Isomerization.
Anne-Frédérique PécharmanMichael S HillClaire L McMullinMary F MahonPublished in: Angewandte Chemie (International ed. in English) (2017)
Reactions of a magnesium-based pinacolatoboryl nucleophile with the electrophilic organoboranes, 9-BBN and Ph3 B, provide facile B-B' single bond formation. Although the Ph3 B derivative is thermally stable, when heated, the unsymmetrical diborane(5) anion derived from 9-BBN is found to isomerize to two regioisomeric species via a proposed mechanism involving dehydroboration of the borabicyclo[3.3.1]nonane and syn-diboration of the resultant alkenyl carbocycle.