Arenes sulfonation

E The writing has again been revised at the sentence level, streamlining the presentation, improving explanations, and updating a thousand small details. Several little-used reactions have been deleted (the alkali fusion of arene-sulfonic acids to give phenols, for instance), and a few new ones have been added (the Sharpless enantioselective epoxidation of alkene.s, for instance). 

D. Arene Sulfonate-Arylsulfone (Sulfone-Fries) Rearrangement.171... 

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

Although anaerobic desulfonation of arene sulfonates, in which the sulfonate is used as a source of sulfur, has been described in a Clostridium sp., the product was not identified (Denger et al. 1996,... 

The specific structure of [(H20)5Ni(py)]2+ was observed in the complexes with the second-sphere coordination of calix[4]arene sulfonate.715 There are two different [(H20)5Ni(py)]2+ cations in the complex assembly. In one the hydrophobic pyridine ring is buried in the hydrophobic cavity of the calixarene with the depth of penetration into the calixarene cavity being 4.3 A (Figure 9). The second independent [(H20)5Ni(py)]2+ cation is intercalated into the calixarene bilayer. 

Figure 9 Complex assembly of [(H20)5Ni(py)]2+ and calix[4]arene sulfonate.715...

Hydrotopy is the phenomenon by which otherwise water-insoluble compounds can be solubilized in the aqueous solution of some compounds, e. g. arene sulfonates. These compounds, known as hydrotopes, are readily water-soluble. The aqueous concentrated solutions (20 to 50%) of the hydrotopes can significantly increase the water solubility of many water-insoluble compounds. 

The formation of organic fluorides has been a difficult undertaking. However, an investigation of the effect of the solvent, leaving group, and source of the fluoride ion has shown that using tetrabutylammonium fluoride or CsF in r-amyl alcohol is able to convert arene sulfonates into fluorides rapidly at 90 °C in excellent yields (>80%).65 Since the half-life of 18F is only 110 min, this is an important advance as it allows one to label compounds with 18F for PET studies. 

M. J. Bowden and E. A. Chandross. 1975. Poly(vinyl arene sulfones) as novel positive photoresists. Journal of the Electrochemical Society 122 1370-1374. 

Klunder, J. M. Onami, T. Sharpless, K. B. Arene sulfonate derivatives of homochiral gly-cidol versatile chiral building blocks for organic synthesis. J. Org. Chem. 1989, 54, 1295-1304. 

Calixarene-based M5 [calix[4]arene sulfonates] vH20 (M = Na x= 12) K (v = 8) Rb (x = 5) Cs (x = 4J) have been used to construct supramolecular assemblies. They have been structurally characterized, and exist as bilayers of anionic truncated pyramids in the cone configuration ... 

The less reactive chlorobenzene and arene sulfonates coupled with phenylindole in the presence of a palladium catalyst generated from X-phos (31, Figure 8). For example, 4-tezt-butylphenyl tosylate reacted to give quantitative yields of ZV-(4-tezt-butylphenyl)indole in the presence of 2 mol% Pd, 5 mol% X-phos and K3PO4 as the base98. 

Na8 calix[6]arene sulfonate which shows no preorganization into a pseudo-planar hexacoordinate structure. 

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