Abstract
Product distribution, total quenching rate ( k T), and rate of chemical reaction ( k r) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C–S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.
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