Of alkyl sulfonates

The Julia-Lythgoc olefination operates by addition of alkyl sulfone anions to carbonyl compounds and subsequent reductive deoxysulfonation (P. Kocienski, 1985). In comparison with the Wittig reaction, it has several advantages sulfones are often more readily available than phosphorus ylides, and it was often successful when the Wittig olefination failed. The elimination step yields exclusively or predominantly the more stable trans olefin stereoisomer. 

The mechanisms by which sulfonate esters undergo nucleophilic substitution are the same as those of alkyl halides Inversion of configuration is observed m 8 2 reac tions of alkyl sulfonates and predominant inversion accompanied by racemization m 8 1 processes... 

The total yield of radicals produced by irradiation of alkyl sulfones at 77 K was estimated65 by comparison of the areas of the absorption peaks with that of a known amount of diphenylpicrylhydrazine to be G(radicals) 2.0. 

Although quite extensive use of has been made in studies on the degradation of alkyl sulfonates (Hales et al. 1986), C1 has achieved only limited application on account of technical difficulties resulting from the low specific activities and the synthetic inaccessibility of appropriately labeled substrates. One of the few examples of its application to the degradation of xenobiotics is provided by a study of the anaerobic dechlorination of hexachlorocyclohexane isomers (Jagnow et al. 1977), the results of which are discussed in Chapter 7, Part 3. 

Jiang, S.X., Liu, X. (1997). Reverse phase HPLC analysis of alkyl sulfonates with nonsuppression conductivity detection. J. Liq. Chromatogr. Related Technol. 20(13) 2053-2061. 

A class of enzymes capable of removing sulfur from alkane sulfonates exists, which may have relevance in microbial desulfurization of alkyl sulfides. A gene cluster ssuEADCB was identified in E. coli. The enzyme SsuD was capable of conversion of pentane sulfonic acid to pentaldehyde and sulfite. It was reported to be capable of conversion of alkyl sulfonates from C2 to CIO, as well as substituted ethanesulfonates and sulfonated buffers. The SsuE was a flavin-reducing enzyme that provided FMNH2 to the SsuD. 

LC separation applying ion chromatography in combination with ion spray mass spectrometric detection was applied for the examination of a synthetic mixture of alkyl sulfonates (CnH2n+i-SO3 re = 8) and AS with different alkyl chain lengths in the selected ion monitoring (SIM) ESI-MS(—) mode [53], Selected ion current profiles provided the separation of the compounds. The ionic matrix constituents of the eluent were removed by a suppressor module prior to MS detection to improve the signal to noise (S/N) ratio. 

Somasundaran, P and D. W. Fuerstenau (1966), "Mechanisms of Alkyl Sulfonate Adsorption at the Alumina-Water Interface", J. of Physical ChemistrylQ, 90-96. 

When chromatographic resolution of species based on modifications located at the protein surface is desired, it may be advisable to use conditions that favor retention of native conformation.17 Here, the standard acidic conditions described in the preceding text may be inappropriate, and mobile phases buffered near neutrality may be required. Buffers based on ammonium acetate, ammonium bicarbonate, and triethylammonium phosphate may prove more useful in resolving polypeptide variants with differing posttranslational modifications, amino acid substitutions, or oxidation and deamidation products. The addition of more hydro-phobic ion-pairing agents may be needed to obtain polypeptide retention, and a variety of alkyl sulfonates and alkyl amines have been described for specific applications.17... 

Combinations of alkyl sulfonic acids from C5 to C8 were tested and the most efficient separations were achieved by running a gradient from 50 6 C6 plus 50 6 C7 to 100 6 C7. Use of the mobile phase compositions illustrated on Table I with the gradient shown on Figure has provided efficient separations for all of the toxins except C1 and C2. Small changes in mobile phase composition and/or gradient profile may be necessary to achieve the desired separations on any particular column or HPLC system. 

Palladium catalysts, 230 of alkyl silyl ethers to alkanes Nickel boride, 197 of alkyl sulfonates to alkanes Lithium triethylborohydride, 153 of alkynes to cis-alkenes... 

The process of obtaining alkyl sulphonate in an autoclave with a mixer has been studied. Basic reagents were water solution of sodium hydrosulfite 36-38% and industrial olefin fractions at 240-320 °C. NaN03 and oxygen from air were used as initiators of the reaction of free radicals. System factors are x, reaction time, h x2 temperature of reaction, °C x3 mole ratio of sodium hydrosulfite and olefin x3 mole ratio of NaN03 and olefin x5 volume ratio of N-propanol and olefin. System response is a yield of alkyl sulfonate as a per cent of theoretical yield. FRFE design... 

Somasundaran, P. and Furstenau, D.W., Mechanisms of alkyl sulfonate adsorption at the alumina-water interface, J. Phys. Chem., 70, 91, 1966. 

Another regiospecific preparation of trimethylsilyl enol ethers involves treatment of acyltrimethylsilanes with the lithium anions of alkyl sulfones or nitriles. In this case, the sulfone or nitrile group is eliminated during the silyl alkoxide rearrangement (e.g., 5 — 6). Mixtures of olefin stereoisomers are obtained. Note that 4 and 8 give complementary regiochemical results. 

Alkyl sulfonates offer a very real advantage over alkyl halides in reactions where stereochemistry is important this advantage lies, not in the reactions of alkyl sulfonates, but in their preparation. Whether we use an alkyl halide or sulfonate, and whether we let it undergo substitution or elimination, our starting point for the study is almost certainly the alcohol. The sulfonate must be prepared from 4he alcohol the halide nearly always will be. It is at the alcohol stage that any resolution will be carried out, or any diastereomers separated the alcohol is then converted into the halide or sulfonate, the reaction we are studying is carried out, and the products are examined. 

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