Tetrahedron

Reaction of singlet oxygen with some benzylic sulfides

SM Bonesi, M Fagnoni, S Monti, A Albini

Index: Bonesi, Sergio M.; Fagnoni, Maurizio; Monti, Sandra; Albini, Angelo Tetrahedron, 2006 , vol. 62, # 46 p. 10716 - 10723

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Citation Number: 18

Abstract

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) 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 ...

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