The rearrangement of exo-2-bromobicyclo[2,2,1]heptane-1-carboxylic acid during reduction with lithium aluminium hydride

Abstract

Contrary to a previous report, endo-2-hydroxymethylbicyclo[2,2,1]heptane is not the only product of reduction with lithium aluminium hydride of exo-2-bromobicyclo[2,2,1]heptane-1-carboxylic acid. The reduction product has been identified as a mixture of endo- and exo-2-hydroxymethylbicyclo[2,2,1]heptane and 1-hydroxymethylbicyclo[2,2,1]heptane. Evidence for the common intermediacy of exo-2-bromo-1-hydroxymethylbicyclo[2,2,1]heptane is presented.