IODINE MONOCHLORIDE OXIDATION OF THIOLS AND SULFENYL IODIDES

"The quantities of initial reactants and the time of mixing were critical. Too long a reaction time or too great an excess of ICL carried the final products well beyond 3 (sic., the sulfenyl iodide)."

"Reactions of 3. A. Photolysis.-In the preliminary study (see Discussion), a solution of 0.0003M in both 4 and I₂ in methylcyclohexane was irradiated. The uv spectrum was compared periodically with spectra of separate control solutions of I₂ and 4. No indication of the characteristic absorption of 3 (280, 444 nm) could be seen. It was soon found that 3 from procedure B (~0.002N) when thus irradiated decomposed immediately (cf. Figure 1 and Discussion)."

• Field, L. Vanhorne, J.L., and Cunningham, L.W. Biologically Oriented Organic Sulfur Chemistry. V. Alkanesulfenyl Iodides. J. Org. Chem. 35(10): 3267-3273 (1970).