1,(ω-1)-Dienes: solvent controlled unilateral or bilateral metallation

Article abstract of DOI:10.1016/0022-328X(91)86133-B

In hexane, i.e. under heterogeneous conditions, 1,(ω-1)-dienes readily undergo double deprotonation to give bis(allylmetal) intermediates.In tetrahydrofuran at -75 or -50 deg C, however, only monometallation occurs with dienes having chains of up to 12 carbon atoms.The practical potential of such selective monosubstitution reactions is demonstrated by two novel pheromone syntheses.