Alkene- 1-sulfonate

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). 

Sulfur trioxide reactivity can also be moderated through the use of SO adducts. The reactivity of such complexes is inversely proportional to their stabihty, and consequentiy they can be selected for a wide variety of conditions. Whereas moderating SO reactivity by adducting agents is generally beneficial, the agents add cost and may contribute to odor and possible toxicity problems in derived products. CeUulosic material has been sulfated with SO.—trimethyl amine adduct in aqueous media at 0 to 5°C (16). Sulfur trioxide—triethyl phosphate has been used to sulfonate alkenes to the corresponding alkene sulfonate (17). Sulfur trioxide—pyridine adduct sulfates oleyl alcohol with no attack of the double bond (18). 

Hashimoto et al. [122-126] have used 13C-NMR as a tool for the determination of sulfonic acid and sulfonate species in AOS and its intermediates. The Na salts of C16 1-alkenesulfonic acid, Cu 2-alkenesulfonic acid, C18 9-alkene-sulfonic acid, 1-propylenesulfonic acid, and C16 3-hydroxyalkanesulfonic acid showed that alkenyl protons in 1-alkenesulfonic acids had NMR chemical shifts at 6.1-6.7 ppm, while other acids had chemical shifts at 5.4-5.9 ppm. The results were useful for rapid determination of 1-alkenesulfonic acid content. 

The surfactants described or characterized for waterflooding are summarized in Table 16-2. Conunercial alkene sulfonates are a mixture of alkene sulfonate, hydroxy alkane sulfonate, and olefin disulfonate [211]. 

Wilkinson s catalyst has also been utilized for the hydroboration of other alkenes. Sulfone derivatives of allyl alcohol can be hydroborated with HBcat and subsequently oxidized to give the secondary rather than primary alcohol. This reactivity proves to be independent of substituents on the sulfur atom.36 Similarly, thioalkenes undergo anti-Markovnikoff addition to afford a-thioboronate esters.37 The benefits of metal-catalyzed reactions come to the fore in the hydroboration of bromoalkenes (higher yields, shorter reaction times), although the benefits were less clear for the corresponding chloroalkenes (Table 3).38,39 Dienes can be hydroborated using both rhodium and palladium catalysts [Pd(PPh3)4] reacts readily with 1,3-dienes, but cyclic dienes are more active towards [Rh4(CO)i2].40... 

The application of collision-induced dissociation (CID(—)) to re-alkane- or linear (primary) alkyl sulfonates (PASs CraH2n+1-S03) or their isomers, the SASs with the modified formula CH3—(CH2)n— CIKSO3)—(CH2)X—CH3, and alkene sulfonates using FIA—MS—MS(—) conditions leads to only one, not quite specific, fragment ion at m/z 80,... 

Fig. 2.11.3. APCI-FIA-MS(-) overview spectrum of an alkene sulfonate blend (general formula C H2 -i-S03H) [22]. 

An enantioselective synthesis of (+)-estradiol has been accomplished from 1,3-dihy-drobenzo[c]thiophene 2,2-dioxide (306) by successive thermal S02-extrusion and cycloaddition (80HCA1703). Treatment of the optically active iodide (307) with two mole equivalents of the masked quinodimethane (306) in the presence of two mole equivalents of sodium hydride gave (308) as a 1 1 mixture of diastereoisomers. Thermolysis of this alkenic sulfone in 1,2,4-trichlorobenzene furnished the trans-anti-trans steroid (309) in 80% yield. Treatment of (309) with methyllithium gave the methyl ketone, which was subjected to a Baeyer-Villiger oxidation and then silyl ether-acetate cleavage to afford (-l-)-estradiol (310 Scheme 66). 

The treatment of /3-sultones with hydrochloric acid results in ring-opening products and is initiated by protonation of the ring oxygen atom. For example, Scheme 12 highlights the conversion of the /3-sultones 53 into the corresponding 2-chlorosulfonic acids 54 and the (E)- and (Z)-alkene-sulfonic acids 55 when exposed to HC1 <1999EJ091>. 

PHOSPHORANES and the Wittig reaction 16-43 SULFONATE ESTERS alkenes + sulfonic acids 15-06... 

Thermal decomposition of 1-alkene polysulfones yields mainly the respective monomers. Cyclic alkene sulfones and 2-alkene sulfones undergo a more complex... 

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