The mechanism of the heterogeneous catalytic monooxidation of thiophene derivatives at the S position by hydrogen peroxide

Nagieva, I. T.

doi:10.1134/s0036024409110119

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“…The other methodology involves an oxidation of a thiophene with either a peracid in the presence of a Lewis acid such as titanium tetrachloride (TiCl 4 ) [43] or boron trifluoride etherate (BF 3 ÁEt 2 O) [44,45] or with hydrogen peroxide in the presence of a protonic acid such as trifluoroacetic acid [46,47] (Scheme 16). Also, the use of the reaction system H 2 O 2 in presence of NaFe(III) ethylenediaminetetraacetate/Al 2 O 3 has been reported [48,49] . The thiophene S-oxides 65, suitably substituted, can be isolated by column chromatography and can be held in substance for a number of weeks without appreciable degradation, when in crystallized form and when kept in the dark.…”

Section: Preparation and Isolation Of Pure Thiophene S-oxidesmentioning

confidence: 99%

Thiophene S-Oxides

Thiemann

Dongol

2019

Chalcogen Chemistry

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Thiophene S-oxides constitute a class of molecules that have been studied in more detail only recently. Their existence as intermediates in the peracid mediated oxidation of thiophenes to thiophene S,S-dioxides, however, has been known over some time. Over the last 20 years, a larger number of thiophene S-oxides have been prepared and isolated in pure form. Thiophene S-oxides have been found to be good dienes in [4 + 2]-cycloaddition reactions, where they react with electron-poor, electron-neutral and electron-rich dienophiles with high syn π-facial stereoselectivity. Thiophene S-oxides have been found to be metabolites of thienyl-containing pharmaceuticals such as the anti-platelet drugs ticlopidine and clopidogrel. The chapter gives an overview of the preparation and reactivity of this class of compounds.

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