1,1-Disulfones alkylation

Later, the same protocol was applied to the polycondensation of aliphatic diols of isosorbide with 1,8-dimesyloctane and other dibromo- and disulfonated alkylating agents... 

A.lpha-Olefm Sulfonates. Sulfonation of alpha-olefins yields a mixture of alkene sulfonates, hydroxyalkane sulfonates, and some amount of various disulfonates. These detergents are excellent foamers with good detergency properties. They are unaffected ia hard water and thek effects are considered superior to the alkyl ether sulfates (9). 

Specialty sulfonic acid-based surfactants make up a rather large portion of surfactant production in the United States. Approximately 136,000 metric tons of specialty sulfonic acid-based surfactants were produced in 1992, which included alpha-olefin sulfonates, sulfobetaines, sulfosuccinates, and alkyl diphenyl ether disulfonates (64). These materials found use in the areas of household cleaning products, cosmetics (qv), toiletries, emulsion polymerization, and agricultural chemical manufacture. 

The condensation of 6 methoxy-1-vinyl-l-tetralol with 2-ttifluoromethyl-l 3 cyclopentanedione in the presence of a small amount of triethylamine produces a secodione (equation 104) This dione is an intermediate in the total synthesis of 13-tnfluoromethyl estrogens, such as 18,18,18-tnfluoro 17(3 estradiol [121] Regwselecnve alkylation of a fluorinated (3-disulfone occurs at low tempera ture [122] (equation 105)... 

AOS is a complex mixture of different chemical species. A typical product composition is as follows [1-7] sodium alkenesulfonate (60-70%) sodium hydroxyalkanesulfonate (30%) sodium disulfonate (0-10%) 6- or 1, 4-sultone (50 ppm) unsulfonated matter (less than 2%) and inorganic salt (mainly sodium sulfate, less than 2.5%). AOS can therefore be regarded as a surfactant system in contrast with other common surfactants such as alkyl sulfates, alkyle-thoxy sulfates, alkanesulfonates, and alkylbenzenesulfonates, which consist of mixtures of their isomers and/or homologs. 

Other disulfones like (32) and (33) were studied (see Ref [6]). They exhibit surprisingly stable anion radicals (and even a stable dianion with (32)). Such charged species could be used as redox mediators, tiowever, reduction of alkyl halides RX by (33) did not permit the formation of alkylated products presumably because of the strong steric strain induced by alkylation of the corresponding carbon atoms in the cyclobutene ring. 

Adsorption of a surfactant on solids is dependent, among other things, on the structure of both the hydro-phobic and hydrophilic portions of it. There are a number of mechanisms proposed for surfactant adsorption and an understanding of the effects of the structure of the surfactant can help in elucidating the role of these mechanisms. In this study, the effect on adsorption on alumina of some structure variations of sulfonates (chain length and the branching and the presence of ethyoxyl, phenyl, disulfonate and dialkyl groups) is examined above and below CMC as a function of surfactant concentration, pH and salinity. Co-operative action between an ionic alkyl sulfonate and a nonionic ethoxylated alcohol is also studied. 

A remarkable stereospecific dehydrative alkylation of (3-disulfones was reported by Falck et al. [406] under Mitsunobu conditions (triethyl phosphine, diethyl azodicarboxylate). The synthesis of a pheromone component of the lesser tea tortrix emphasizes some of the possibilities offered by coupling this reaction with further uses of the sulfone functionality. In the present case, monodesulfonylation with lithium naphthalenide (-78°C, 5 min), in situ alkylation (-78 to 23°C, 1 h), and Li-naphthalene cleavage of the second sulfonyl group (—78°C, 5 min) yielded in a one-pot procedure a THP ether which was converted into the sought after pheromone through direct acetylation. 

In contrast, copper (II) triflatc effects oxidative dimerization of a-anions of n-alkyl sulfones to a-disulfones (meso- and dl- isomers). Coupling of a-anions of allylic sulfones with this catalyst occurs mainly at the /-position.2... 

A series of tetrasubstituted sulfoxonium ylides 89a-h were synthesized from 83 in a two-step reaction via 2,4-disubstituted disulfones 88a-h, which were converted into the final ylides upon reactions with very strongly silylating agents, such as C4F9-SO2-OR, where R = Si(Alkyl)3 (Scheme 10) <1996CB161>. 

Dianions of alkyl-substituted sulfoxonium ylides 91a,b,e,f were prepared from 83 also by a two-step procedure via 2,4-dialkylated disulfones 90a-g. Deprotonation of 83 and alkylation yielded a family of bis-sulfones 90a-g, which upon a second deprotonation by treatment with an appropriate base were converted into the corresponding salts 91a,b,e,f (Scheme 11) <1996CB161>. 

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