Single-Electron Transfer in the Reaction of Red Phosphorus with 4-(Phenylsulfanyl)benzophenones in Superbase Systems MOH/DMSO

Abstract

Red phosphorus reacted with 4-(phenylsulfanyl)- and bis(4-phenylsulfanyl)benzophenones in superbase suspensions MOH/DMSO (M = Na, K) on heating at (85°C, 1.5–4 h, argon atmosphere) according to the single-electron transfer mechanism. The formation of potassium bis{phenyl[4-(phenylsulfanyl)phenyl]­methyl} phosphate radical anion was detected by ESR spectroscopy. Reduction products of the initial (phenylsulfanyl)benzophenones (diarylmethanols and diarylmethanes functionalized with phenylsulfanyl groups) and diphenyl disulfide were isolated from the reaction mixtures, while potassium bis{phenyl[4-(phenylsulfanyl)phenyl]methyl} and bis{di[4-(phenylsulfanyl)phenyl]methyl} phosphates were detected among the products and identified by NMR spectroscopy).