1 - Alkoxy alkyl sulfonates

Hydroxy- bzw. 2-Alkoxy-alkyl)-phenyl-sulfone konnen in DMF in Gegenwart von Essigsaure Oder Phenol als Protonendonator an Quecksilber kathodisch an der S-CAlkyl-Bindung unter Bildung von Olefinen (bis 90% d. Th.) gespalten werden. Mit zunehmender Protonendonator-Konzentration nimmt der Anteil des Alkans zu (bis zu 40% d.Th.) ... 

Alkylation of the hydroxy aromatic compound to the corresponding alkoxy aromatic compound may be performed in accordance with known alkylation procedures in which the hydroxy aromatic compound is reacted with an alkyl sulfate, alkyl halide or alkyl sulfonate in a suitable solvent, usually water, containing a base such as sodium hydroxide. Such reactions are shown at various places in the literature, as for ex. in Organic Synthesis, Col. Vol. II, page 619, 1943, in which veratraldehyde is prepared from vanillin. The iodide salt may, if desired, be recaptured subsequent to the alkylation reaction. 

The solubility of polythiophenes has also been increased by attaching alkoxy groups to bithiophere monomers.12 Other workers131415 have been concerned with producing pyrroles and thiophenes with alkyl-sulfonated chains attached to increase the water solubility of the polymer. 

Synthesis of (+)-Chatancin. The alkylation of an a-sulfonyl carbanion derived from a y-alkoxy functionalized sulfone with an allylic bromide and subsequent reductive desulfonylation with Na/Hg constitutes a key step in the synthesis of the marine diterpene (+)-chatancin (Eq. 144).251... 

Soluble conducting polymers can be solvent cast to form coatings. The addition of appropriate substituents to the polymer backbone or to the dopant ion can impart the necessary solubility to the polymer. For example, alkyl or alkoxy groups appended to the polymer backbone yield polypyrroles [117,118], polythiophenes [118], polyanilines [119,120], and poly(p-phenylenevinylenes) [97] that are soluble in common organic solvents. Alternatively, the attachment of ionizable functionalities (such as alkyl sulfonates or carboxylates) to the polymer backbone can impart water solubility to the polymer, and this approach has been used to form water-soluble polypyrroles [121], polythiophenes [122], and polyanilines [123]. These latter polymers are often referred to as self-doped polymers as the anionic dopant is covalently attached to the polymer backbone [9]. For use as a corrosion control coating, these water-soluble polymers must be cross-linked [124] or otherwise rendered insoluble. 

PPy S alkyl S alkoxy S hydroxyalkyl S caiboxyalkyl S alkyl sulfonic add S amine S ester group... 

Procedure for the coupling of the alkyl sulfone and the aldehyde to generate the a-alkoxy sulfone. 

Nucleophilic Substitution of Optically Active l-Alkoxy(polyfluoro)alkyl Sulfonates... 

Ph) or OPh, the last two of which may be substituted by up to three groups selected from alkyl, alkoxy, sulfonate, carboxylate, alkylthio-,... 

Tnfluoroacetic anhydnde in a mixture with sulfuric acid is an efficient reagent for the sulfonylation of aromatic compounds [44] The reaction of benzene with this system in nitromethane at room temperature gives diphenyl sulfone in 61% yield Alkyl and alkoxy benzenes under similar conditions form the corresponding diaryl sulfones in almost quantitative yield, whereas yields of sulfones from deactivated arenes such as chlorobenzene are substantially lower [44] The same reagent (tnfluoroacetic anhydride-sulfunc acid) reacts with adamantane and its derivatives with formation of isomeric adamantanols, adamantanones, and cyclic sultones [45]... 

In addition to alkyl-substituted derivatives, soluble PPPs 6 are also known today containing alkoxy groups as well as ionic side groups (carboxy and sulfonic acid functions) [18]. Schliiter et al. recently described the generation of soluble PPPs decorated with densely packed stcrically demanding dendrons on the formation of cylindrically shaped dendrimers, so-called cylinder dendrimers ] 19]. 

A. Alkyl and alkoxy sulfonates Fatty alcohols and amides Glycols and glycol ethers... 

Substituents such as long-chain alkyl, alkoxy, or alkylamino groups and also sulfonic acid functions tend to increase solubility. 

The reductive lithiation of a-alkoxy phenylsulfides is a slow process (typically 0.5-1 h at -78°C) and lowering the LUMO of the electron acceptor by using, for example, an anomeric sulfone, leads to a much faster electron transfer [11]. Reductive lithiation of sulfone 22 is fast (less than 1 min) and leads to similar a-lithio reagents to those described above and Scheme 8 shows examples of simple a-C-2-deoxyglycosides 23 and 24 prepared by this protocol. The most interesting feature of anomeric sulfones is that alkylation prior to the reductive desulfonylation event is achievable. In this way, a one-pot four-step sequence... 

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