CONCERNING THE REDUCTION OF ALKYL HALIDES BY LiAlH4. EVIDENCE THAT AlH3 PRODUCED IN SITU IS THE ONE ELECTRON TRANSFER AGENT.

Article abstract of DOI:10.1016/S0040-4039(00)88034-X

The reduction of 1⁰ and 2⁰ alkyl iodides by LiAlH4 has been shown to involve a radical intermediate formed by the reaction of the alkyl iodide with the AlH3 and LiI produced in situ in conjunction with LiAlH4 rather than by LiAlH4 alone, as evidenced by cyclized products in the reduction of 6-iodo-1-heptene, by the trapping of the radical and by stereochemical studies of the 2-halooctanes.