THE RELATIVE REACTIVITY OF THIOETHERS AND SULFOXIDES TOWARD OXYGEN-TRANSFER REAGENTS - THE CASE OF DIOXIRANES

被引：20

作者：

BALLISTRERI, FP ^{[1
]}

TOMASELLI, GA ^{[1
]}

TOSCANO, RM ^{[1
]}

BONCHIO, M ^{[1
]}

CONTE, V ^{[1
]}

DIFURIA, F ^{[1
]}

机构：

[1] UNIV PADUA,CNR,CTR STUDIO MECCANISMI REAZ ORGAN,DIPARTIMENTO CHIM ORGAN,I-35135 PADUA,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 43期

关键词：

D O I：

10.1016/S0040-4039(00)78418-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the competitive oxidation of thioethers and sulfoxides by electrophilic reagents the reactivity ratio may be small enough to cause the formation of mixtures of products. This has been studied in the reaction of dimethyldioxirane, DMD, and trifluoromethyl-methyldioxirane, TMMD. In particular TMMD oxidizes both thioethers and sulfoxides whereas DMD attacks only thioethers. By applying the logic which has been used to develop mechanistic probes based on such competitive oxidations, the unrealistic conclusion that TMMD is less electrophilic than DMD would be reached On the contrary we show also by means of Hammett plots on substituted sulfoxides that DMD and TMMD are both electrophilic oxidants toward sulfoxides and that TMMD is less selective than DMD being a stronger oxidant.

引用

页码：8041 / 8044

页数：4

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