Vitamin B12-catalyzed conversion of some γ- and δ-bromoalkanols to polyhydroxy alkanols

Vitamin B₁₂-catalyzed allylic dimerization of some γ- and δ-bromoalkanols with activated Zn-dust in mixture ethanol/water (1:1) has been studied. Investigated bromoalkanols were prepared from corresponding tertiary Δ⁴- and Δ⁵-alkenols by means of benzeneselenyl bromide and subjected to chemical reduction with vitamin B₁₂. All investigated bromoalkanols, after dehydrobromination, underwent to oxidative allylic coupling and hydratation in the presence of protic solvents to give predominantly polyhydroxy alkanols.