Aryl sulfones

D. Arene Sulfonate-Aryl Sulfone (Sulfone-Fries) Rearrangement71... 

Hodgdon, R. B. and Hay, A. S. 1970. Sulfonated aryl-substituted polyphenylene ether ion exchange membranes. US Patent 3,528,858. 

Water-soluble phosphines containing sulfonated aryl and alkyl side chains. 

Simple alkencs that do undergo the Diels-Alder reaction include conjugated carbonyl compounds, nitro compounds, nitriles, sulfones, aryl alkenes, vinyl ethers and esters, haloalkenes, and dienes. In addition to those you have seen so far, a few examples are shown in the margin. In the last example it is the isolated double bond in the right-hand ring that accepts the diene. Conjugation with the left-hand ring activates this alkene. But what exactly do we mean by activate in this sense We shall return to that question in a minute. 

Diaryl sulfones. Aryl sulfonyl bromides (but not sulfonyl chlorides) react with silver trifluoromethanesulfonate in nitromethane at 0° to form unstable mixed sulfonic anhydrides (c/ 4, 533-534). These react with arenes (threefold excess) at the same temperature to give diaryl sulfones usually in yields of 80-100%. 

Simple alkenes that do undergo the Diels-Alder reaction include conjugated carbonyl compounds, nitro compounds, nitriles, sulfones, aryl alkenes, vinyl ethers and esters, haloaUc-... 

The sulfonation of triphenyl phosphine with fuming sulfuric acid can give three possible products monosulfonated triphenylphosphine (TPPMS), disulfonated triphenylphosphine (TPPDS), and TPPTS 1, depending on the reaction conditions (Figure 9). Using this method many sulfonated aryl phophines have been prepared (2b,... 

Perrot C, Gonon L, Bardet M, Marestin C, Pierre-Bayle A, Gebel G, et al. Degradation of a sulfonated aryl ether ketone model compound in oxidative media (sPAEK). Polymer 2009 50(7) 1671-81. 

Chang et al. [185] prepared SPAE ionomers, xx-PSU-Sn (where xx=mol.% of the sulfonic acid group in the PSF repeating unit= 135,160, and 200. respectively) with three different types of acidic groups (fluoroalkyl sulfonic, aryl sulfonic, and alkyl sulfonic acids), as shown in Scheme 2.52 for low-RH, high-temperature PEMFC applications. 

Sulfidation can occur with simple sulfur components as can be present in syngas or propene (H,S, COS), but also as a result of breakdown and reduction of the sulfonate groups of sulfonated aryl-Ugands). 

Simply mixing solutions of the tetracationic diphosphine (175) with a tetraanionic calix[4]arene leads to the formation of supramolecular heterocapsules that can bind a transition metal ion within the cavity of the assembly, providing a new class of potential supramolecular catalysts. Sulfonated aryl-phosphines and -diphosphines form supramolecular adducts with cyclodextrins that are also of interest as new ligand systems,and the mechanism of such inclusion processes has attracted a theoretical study. ... 

When the polar sulfonated aryl group is replaced by the nonpolar alkyl group, its water solubility and thus the recyclability are lost. 

Water may not only dissolve the catalyst but also act as a moderator (e.g., by enhanced hydrogen-bonding properties which lead to more and subtle polarization) [33]. Moreover, the degradation of ligands can be facilitated, as observed in the oxidation of a sulfonated aryl phosphine to a phosphine oxide in the coordination sphere of rhodium (Scheme 7.3 see also Section 2.1.6). 

Polymer blend membranes comprising a functional polymer based on sulfonated aryl polymers are used as polymer electrolyte membranes in fuel cells, in particular in low temperature fuel cells (37). The polymers tend to be brittle and the addition of a plasticizer which reduces the brittleness of the polymers is advantageous. 

Glipa et al. [55] successfully grafted sulfonated aryl groups onto m-PBI, leading to a proton conducting polymer with various degrees of sulfonation... 

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