Thiophene 1,1‐Dioxides, Sesquioxides, and 1‐Oxides

Raasch, Maynard S.

doi:10.1002/9780470187234.ch7

Cited by 9 publications

(1 citation statement)

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“…Much of the early work on the oxidation of thiophenes to thiophene S,S-dioxides involved hydrogen peroxide (H 2 O 2 ) as oxidant, later meta-chloroperoxybenzoic acid (m-CPBA). That thiophene S-oxide was an intermediate in such oxidation reactions [6][7][8] was evident from the isolation of so-called sesquioxides as dimerization products of thiophene S-oxides [9][10][11][12]. Here, the thiophene S-oxide acted as diene with either another molecule of thiophene S-oxide or thiophene S,S-dioxide acting as ene [9][10][11][12] to give cycloadducts 6-8 ( Figure 2).…”

Section: Early History Of Oxidation Reactions Of Thiophenes: Cycloaddmentioning

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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Section: Early History Of Oxidation Reactions Of Thiophenes: Cycloaddmentioning

confidence: 99%

Thiophene S-Oxides

Thiemann

Dongol

2019

Chalcogen Chemistry

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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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