Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy(6)Pb(2) (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy•). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)(2) and (PhTe)(2), the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)(2). This probably occurred due to the low carbon-radical-capturing ability of (PhS)(2) and the high photosensitivity of the cyclohexyl-tellurium bond.