Phenyl methyl ketone sulphoxide

In the course of this study, the authors determined /Lvalues for dibenzyl, methyl phenyl, methyl p-nitrophenyl, di-p-tolyl, di-isopropyl and tetramethylene sulphoxides and for diethyl, dipropyl and dibutyl sulphites. The /Lscales are applied to the various reactions or the spectral measurements. The /Lscales have been divided into either family-dependent (FD) types, which means two or more compounds can share the same /Lscale, family-independent (FI) types. Consequently, a variety of /Lscales are now available for various families of the bases, including 29 aldehydes and ketones, 17 carboxylic amides and ureas, 14 carboxylic acids esters, 4 acyl halides, 5 nitriles, 10 ethers, 16 phosphine oxides, 12 sulphinyl compounds, 15 pyridines and pyrimidines, 16 sp3 hybridized amines and 10 alcohols. The enthalpies of formation of the hydrogen bond of 4-fluorophenol with both sulphoxides and phosphine oxides and related derivatives fit the empirical equation 18, where the standard deviation is y = 0.983. Several averaged scales are shown in Table 1588. 

Hexane. 3500—1300 cm. Thin film 2-Methylpentane. 3500—1300 cm . Thin film Dec-l-ene. 3500—1300 cm. Thin film /rfl 5-Stilbene. 1300—400 cm". KBr disc Styrene. 3500—1300 cm". Thin film Styrene 1300—400 cm". Thin film Phenyl Acetylene. 3500—1300 cm". Thin film Phenyl Acetylene. 1300—400 cm". Thin film Aromatic substitution patterns. 2000—1600 cm" para-Cresol. 3500—1300 cm". I.M. CCI4 solution tert-Butyl methyl ketone. 4000—650 cm". Thin film -Heptaldehyde. 4000—650 cm". Thin film Di-/sopropyl ether. 4000—650 cm". Thin film Acetic Anhydride. 4000—650 cm". Thin film Propionic acid. 4000—650 cm". Thin film Propionic acid. 3500—2000 cm". Solution 0.005M CCI4 Methyl salicylate. 4000—650 cm . Thin film n-Butylamine. 4000—650 cm". Thin film Benzamide. 3500—1300 cm". KBr disc Methionine. 4000—650 cm". KBr disc Benzonitrile. 3500—1300 cm". Thin film Benzonitrile. 1300—400 cm". Thin film A-Methyl acetamide. 3500—650 cm". Thin film Methyl acrylate. 4000—650 cm". Thin film Benzoyl chloride. 4000—650 cm". Thin film Triphenyl phosphate. 3500—1300 cm". Melt Triphenyl phosphate. 1300—400 cm". Melt Di-wopropyl sulphone. 4000—650 cm". Melt Nitrobenzene. 4000—650 cm". Thin film Dimethyl sulphoxide. 4000—650 cm". Thin film Polymeric silicone. 4000—650 cm". Thin film Calcium sulphate Dihydrate. 4000—650 cm". KBr disc... 

Reaction of the carbanion of chloromethyl phenyl sulphoxide 409 with carbonyl compounds yields the corresponding 0-hydroxy adducts 410 in 68-79% yield. Each of these compounds appears to be a single isomer (equation 242). Treatment of adducts 410 with dilute potassium hydroxide in methanol at room temperature gives the epoxy sulphoxides 411 (equation 243). The ease of this intramolecular displacement of chloride ion contrasts with a great difficulty in displacing chloride ion from chloromethyl phenyl sulphoxide by external nucleophiles . When chloromethyl methyl sulphoxide 412 is reacted with unsymmetrical ketones in the presence of potassium tcrt-butoxide in tert-butanol oxiranes are directly formed as a mixture of diastereoisomers (equation 244). a-Sulphinyl epoxides 413 rearrange to a-sulphinyl aldehydes 414 or ketones, which can be transformed by elimination of sulphenic acid into a, 8-unsaturated aldehydes or ketones (equation 245). The lithium salts (410a) of a-chloro-/ -hydroxyalkyl... 

A condensation of vinyl sulphides of synthetic value involves the reaction of a-ethylthio-styrenes with an aldehyde in the presence of a Lewis acid catalyst to give 3-ethylthio-indenes. Regiospecific and stereospecific pentannelation i.e, fusion of a cyclopentane ring) of an alicyclic ketone involves arylthiomethylen-ation followed by base-catalysed addition to an aj8-unsaturated ester. a-Phenyl-thiobutenolides are less reactive Michael acceptors than their sulphoxide counterparts, and /SjS-dichlorovinyl sulphides are less reactive in electrophilic reactions than their oxygen counterparts. Dimerization of aryl a-cyanovinyl sulphides occurs more readily than that of alkyl analogues, since the intermediate 1,4-diradical ArSC(CN)CH2CH2d(CN)SAr, which cyclizes to the cyclobutane, is more stable. Products obtained by photolysis of methyl vinyl sulphide are accounted for by homolysis of both vinyl—S and methyl—S bonds. The kinetics of catalysed cis-trans isomerization of aryl vinyl sulphides have been studied. ... 

---