Sulfone, methyl phenyl

Methyl phenyl sulfide Methyl phenyl sulfoxide Methyl phenyl sulfone... 

FIGURE 15. The ( perpendicular ) torsional form of methyl-phenyl sulfone. The projection formula represents a view along the S—C(phenyl) bond. The other drawing shows the labels of the benzene ring angles. 

TABLE 4. Selected molecular parameters of methyl phenyl sulfone (from gas-phase electron diffraction) and p-methylsulfonylbenzoic acid (from X-ray crystallography)... 

Tanaka and coworkers337 reported successful syntheses of aldehydes and ketones using (l-ethoxyethoxy)methyl phenyl sulfone 258 and 1-(1-ethoxyethoxy)ethyl phenyl sulfone 259, as shown in the following scheme. 

The oxidative dimerization of the anion of methyl phenyl sulfone (from a Grignard reagent) in ethereal solution in the presence of cupric chloride in 5% yield has been reported47. Despite the reported48 poor stability of the a-sulfonyl C-centered radicals, Julia and coworkers49 provoked the dimerization (in 13 to 56% yields) of the lithiated carbanion of alkyl phenyl sulfones using cupric salts as oxidants. The best results are obtained with cupric triflates in THF-isobutyronitrile medium (56% yield for R = H). For allyl phenyl sulfones the coupling in the 3-3 mode is predominant. 

Rossi and Bunnett64 studied the chemical reductive cleavage of diphenyl sulfoxide, diphenyl sulfone and methyl phenyl sulfone under the action of potassium metal in liquid ammonia in the presence of acetone. The enolate ion is used to trap phenyl radicals formed eventually during the process, in order to determine whether one or two electrons are required for the mechanism of cleavage (Scheme 7). In all the runs, phenyl anion is... 

Auch sterische Aspekte konnen eine Rolle spielen. So erhalt man z. B. in DMF/Tetra-butylammoniumperchlorat bzw. in Methanol/Tetramethylammoniumchlorid in geteilter Zelle an Quecksilber aus Methyl-(2-methyl-phenyl)-sulfon 2-Methyl-benzolsulfinsaure (bis 93% d. Th.) bzw. aus Methyl-(2-tert.-butyl-phenyl)-sulfon Methansulfinsaure (bis 91% d. Th.). (2-tert.-Butyl-phenyl)-benzyl-sulfon wiederum wird zur 2-tert.-Butyl-ben-zolsulfinsaure (86% d. Th.) gespalten5. 

Pedersen and coworkers investigated the El mass spectra of several 2-hydroxyphenyl alkyl sulfones (39) and sulfoxides (Section II.B). The methyl derivative seemed to fragment only via sulfinate ester formation giving the primary product ions m/z 157 and 109 (equation 14). Obviously hydrogen bonding between the ortho hydroxyl and the sulfone sulfur makes the loss of CH3SO2 difficult in contrast to the situation in methyl phenyl sulfone. The sulfinate ester rearrangement is not important when R>Et in 39. 

The oxidation of methyl phenyl sulfide using fresh PWAA gave methyl phenyl sulfone in 97% yield. In the repeated use of recovered catalyst, the yields of sulfone in runs 2 to 5 ranged from 82 to 88%. The activities of recovered catalysts were somewhat reduced. The deactivation may be caused by catalyst pulverization or degradation of the PW12O403- species. While the reusability and stability of the catalyst should be improved, this concept would be useful for the creation of sophisticated solid catalysts. After Ikegami s reports, Neumann and coworkers [140] applied this strategy to the development of alkylated polyethyleneimine/POM synzymes. 

Methylphenol, see Phenol Methyl phenyl sulfone, see Fonofos Methyl phosphate, Trichlorfon IV-Methylphosphinic acid, see Glvphosate 2-Methylpropanal, see 2-Methylpropene, 2,2,4-... 

Plant. In plants, fonofos is oxidized to the phosphonothioate (Hartley and Kidd, 1987). Oat plants were grown in two soils treated with [ C]fonofos. Most of the residues remained bound to the soil. Less than 2% of the applied [ C]fonofos was recovered from the oat leaves. Metabolites identified in both soils and leaves were methyl phenyl sulfone, 2-, 3- and 4-hydroyxymethyl phenyl sulfone, thiophenol, diphenyl disulfide, and fonofos oxon (Fuhremann and Lichtenstein, 1980 Lichtenstein et al., 1982). 

After solvent was removed by rotavapor, the crude product was chromatographed over silica gel to afford methyl phenyl sulfones (0.154 g, 99 % yield, white solid). Spectral data were comparable with literature values. 

Similar base-induced rearrangement of 4-(l-bromopentacyclo[4.3.0.02-5.03-8.04,7]nonan-9-onyl ethylene acetal)methyl phenyl sulfone (68) leads also to an almost quantitative yield of l-bromo-4-(benzenesulfonylmethyl)tricyclo[4.2.1.02-5]nona-3,7-dien-9-one ethylene acetal (69), together with a trace amount of l-bromo-4-(benzenesulfonylmethylidene)tricyclo[4.2.1.02,5]-non-7-en-9-one ethylene acetal (70).171... 

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