Reaction of singlet oxygen with some benzylic sulfides

被引：31

作者：

Bonesi, Sergio M.

Fagnoni, Maurizio

Monti, Sandra

Albini, Angelo

机构：

[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy

[2] Univ Buenos Aires, CHIDECAR, CONICET, Dep Org,Fac Cien Ex Nat, RA-1428 Buenos Aires, DF, Argentina

[3] ISOF Inst, CNR, I-40129 Bologna, Italy

来源：

TETRAHEDRON | 2006年 / 62卷 / 46期

关键词：

D O I：

10.1016/j.tet.2006.07.110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

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页码：10716 / 10723

页数：8

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