Atom Transfer Cyclization of Simple Hexenyl Iodides. A Caution on the Use of Alkenyl Iodides as Probes for the Detection of Single Electron Transfer Processes.

Abstract The trialkyltin initiated isomerization of 1-iodo-5-hexene to (iodomethyl)cyclopentane is reported. Rapid and reversible iodine atom transfer between alkyl radicals is the key chain transfer step. The results suggest an important caution in the use of hexenyl iodides as SET probes: a good mechanism exists whereby the yield of rearranged products may be much greater than the amount of radicals produced by the reaction under study!