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Reaction of singlet oxygen with some benzylic sulfides |
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| Authors: | Sergio M. Bonesi Maurizio Fagnoni Angelo Albini |
| Affiliation: | a CHIDECAR-CONICET, Dep. Quim. Org., Fac. Cien. Ex. Nat., Universidad de Buenos Aires, Ciudad Universidaria, 1428 Buenos Aires, Argentina b Department of Organic Chemistry, University of Pavia, v. Taramelli 10, 27100 Pavia, Italy c ISOF-CNR Institute, v. Gobetti 123, 40129 Bologna, Italy |
| 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 efficiency. The behavior of sulfides is compared to that of alkenes and amines. |
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