Reaction of singlet oxygen with some benzylic sulfides.

BONESI SERGIO M., FAGNONI MAURIZIO, MONTI SANDRA, ALBINI ANGELO.

TETRAHEDRON

Pergamon

Lugar: Oxford; Año: 2006 p. 11716 - 11723

0040-4020

Abstract—Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, a-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 a-H abstraction leads to oxidative C–S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.—Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, a-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 a-H abstraction leads to oxidative C–S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.a-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 a-H abstraction leads to oxidative C–S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.a-H abstraction leads to oxidative C–S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines. 2006 Elsevier Ltd. All rights reserved.2006 Elsevier Ltd. All rights reserved.