REDUCTION OF OMEGA-CHLOROPERFLUOROALKYL IODIDES WITH LITHIUM ALUMINUM-HYDRIDE - A SINGLE ELECTRON-TRANSFER PROCESS

The reduction of ω-chloroperfluoroalkyl iodides(1a-b) with LiALH4 gave ω-chloroperfluoroalkyl hydride(3) and α,ω-dihydroperfluoroalkane(4). However, in the presence of olefin, the addition product (6) was obtained. The reaction can be partly suppressed by p-dinitrobenzene (p-DNB), and tetrahydrofuran derivatives were obtained from the reaction of ω-chloroperfluoroalkyl iodides with diallyl ether. A single electron transfer process was proposed. © 1990.