Ethylene sulfones

The simplest monomer, ethylenesulfonic acid, is made by elimination from sodium hydroxyethyl sulfonate and polyphosphoric acid. Ethylenesulfonic acid is readily polymerized alone or can be incorporated as a copolymer using such monomers as acrylamide, aHyl acrylamide, sodium acrylate, acrylonitrile, methylacrylic acid, and vinyl acetate (222). Styrene and isobutene fail to copolymerize with ethylene sulfonic acid. 

In contrast to a, -ethylenic ketones or even a, -ethylenic sulfones, a, ) -ethylenic sulfoxides generally are not sufficiently electrophilic to undergo successful nucleophilic j8-addition . a-Carbonyl-a, j8-ethylenic sulfoxides, however, are potent, doubly activated alkenes which undergo rapid and complete -addition of various types of nucleophiles even at — 78 °C. A brief account summarizing this area is available . The stereochemical outcome of such asymmetric conjugate additions to enantiomerically pure 2-sulfmyl 2-cycloalkenones and 2-sulfinyl-2-alkenolides has been rationalized in terms of a metal-chelated intermediate in which a metal ion locks the -carbonyl sulfoxide into a rigid conformation (36 cf. 33). In this fixed conformation, one diastereoface of the cyclic n... 

The most radiation-stable poly(olefin sulfone) is poly(ethylene sulfone) and the most radiation-sensitive is poly(cyclohexene sulfone). In the case of poly(3-methyl-1-butene sulfone) there is very much isomerization of the olefin formed by radiolysis and only 58.5% of the olefin formed is 3-methyl-l-butene. The main isomerization product is 2-methyl-2-butene (37.3% of the olefin). Similar isomerization, though to a smaller extent, occurs in poly(l-butene sulfone) where about 10% of 2-butene is formed. The formation of the olefin isomer may occur partly by radiation-induced isomerization of the initial olefin, but studies with added scavengers do not support this as the major source of the isomers. The presence of a cation scavenger, triethylamine, eliminates the formation of the isomer of the parent olefin in both cases of poly(l-butene sulfone) and poly(3-methyl-l-butene sulfone) indicating that the isomerization of the olefin occurred mainly by a cationic mechanism, as suggested previously . ... 

Q , 8-Ethylenic sulfones exhibit a behavior that could be considered as specific and totally different from that of Q , 8-ethylenic ketones or nitriles. Thus, with the present series, there is practically no case of dimerization or double-bond saturation. This seems to be because of the fact that reduction of compounds of this series cannot be completed neither in acidic nor in aqueous solutions because a fast cleavage occurs at the level of the anion radical. 

Acrylonitrile N-methylol acrylamide Acrylamide Ethylene sulfonic acid Allyl sulfonic acid Crosslinker (3) Semicrystalline polymers (2)... 

Supersonic gas chromatograph-mass spectrometry (GC-MS) apparently has several advantages over standard GS-MS methods for the detection of thermally unstable molecules <2004JCH233>. A GC and MS are interfaced with a supersonic molecular beam (SMB), and activation of cold compounds in the SMB occurs by electron ionization or cluster chemical ionization. The gas flow rate is very high, permitting the elution of compounds that would normally be degraded. Ethylene sulfone was one of the analytes for which the technique was demonstrated. 

Reaction with ajf-etkykmc sulfimes. Aldehydes and ketones can be transformed into gem-dialkylalkancs (3) by conversion first into the ,/l-ethylenic sulfone (I, see n-BMyllithnn, this volume). This is then treated with a dialkylcopperlithium reagent... 

ETHYLENE KETALS Mercuric acetate. o,d-ETHYLENIC SULFONES n-ButyUith-ium. 

A free radical polymerization reaction in the presence of a peroxide or hydroperoxide can take place between an olefin and SO2. The resulting poly(olefin sulfone) may have a variable composition (variable content of SO2), but poIy(ethylene-a/f-sulfur dioxide), CAS 110711-58-5, or poly(ethylene sulfone) can be obtained. Different olefins can be used in the reaction, as well as butadiene. Poly(sulfur dioxide-co-alkenes) may have a variable composition from 1.1 mole ratio (a/t copolymer) to various other monomer ratios. 

For the reaction of a,/i-ethylenic sulfones with dialkylcopperlithium reagents, see Dimethylcopperlithiuin, this volume. 

Polyperfluoro (ethylene-co-ethylene sulfonic acid) E. I. Du Pont de Nemours, Wilmington, Delaware... 

The formation of thiirane 1,1-dioxides has been extended to the reactions of 3-phenyl-2-propene-l-sulfonyl and those of other arylmethanesulfonyl chlorides158, and recently to primary alkanesulfonyl chlorides159. 1-Octanesulfonyl chloride with triethylamine in acetonitrile at —40 °C, for example, gave an 88% yield of a 76 24 mixture of the trans- and cis-2,3-diheptylthiirane 1,1-dioxides this material on thermolysis at 80-100 °C produced a 75 25 mixture of the ( )- and (Z)-8-hexadecenes (in 76% yield). Methanesulfonyl chloride (in ether at 0 °C) gave a 64% yield of thiirane 1,2-dioxide (ethylene sulfone, 66)159, hitherto only available from reactions with diazomethane109 (see Section IV.D and below). 

Sodium 2-chloroethanesulfonate, ClCH2CH2S03Na, and sodium ethylene sulfonate, CH2=CHS03Na, have been used industrially and in the laboratory to solubilize starch, cellulose, and other compounds by sulfoethylation. 

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