Sir: We report here evidence that the oxidation of alkyl iodides in nonpolar media gives an oxidized iodine intermediate (the iodoso compound) which can lead to olefins by a syn elimination process. It is known that amine oxides, 2 sulfoxide^,^ and selenoxides4 undergo thermal pericyclic eliminations of hydroxylamine, sulfenic acid (RSOH), and selenenic acid (RSeOH), respectively, to form olefins. Alkyl iodide oxides (iodoso compounds), although ...
