Reduction of exo-2-methyl-3, 4-dichlorobicyclo[3.2.1]oct-2-ene and the exo-2-phenyl-3,4-dibromo analogue with lithium aluminium hydride proceeds mainly with allylic rearrangement. Moreover, hydride enters and bromide leaves synfacially. The stereochemistry of the process is discussed in the light of the favourable energy of a quasi-cyclic transition state in which reagent and halide are complexed.