REACTIONS OF 1-HALO-5-HEXENES WITH ALKYLLITHIUMS. EVIDENCE FOR A PRONOUNCED HALOGEN EFFECT ON THE MECHANISM OF THE METAL-HALOGEN INTERCHANGE REACTION OF PRIMARY ALKYL HALIDES

Article abstract of DOI:10.1016/S0040-4039(00)84396-8

Reaction of t-BuLi with 1-halo-5-hexenes and 1-halo-6-methyl-5-heptenes at -78 gradC has revealed that, whereas 1 deg alkyl iodides are cleanly converted to alkyllithiums in a non-radical process, the corresponding 1 deg alkyl bromides undergo interchange at least partially via a radical-mediated, SET pathway.