Hydride transfer reactions in the series of 1-boraadamantane “ate”-complexes

Abstract Lithium 1-alkyl-1-boraadamantanates, obtained from lithium alkyls and the tetrahydrofuran complex of 1-boraadamantane, afford 7-methylene-3-alkyl-3-borabicyclo[3.3.1]nonanes when treated with acetyl chloride. With the use of selectively deuterated lithium [7-D]-1,3,5-trimethyl-1-boraadamantanate, it is shown that the reaction involves the elimination of deuteride ion from the β-carbon atom.