Phenyl sulfone

Low-density polyethylene (LDPE) Poly(phenyl sulfone)... 

Properties Unfilled 20% glass-fiber- reinforced Unfilled 20% glass-fiber- reinforced Poly(ether sulfone) Poly(phenyl sulfone)... 

Sulphenone /5 (9-J(9-, /)-chlorophenyl phenyl sulfone (142), is a white soHd (mp 98°C). The technical material consists of ca 80% of this compound, with small amounts of 0- and y -isomers, bis(/)-chlorophenyl) sulfone, and diphenyl sulfone. Sulphenone is effective against all stages of mites. Its oral LD q to the rat is >2000 mg. 

Condensation of vinyl chloride with formaldehyde and HCl (Prins reaction) yields 3,3-dichloro-l-propanol [83682-72-8] and 2,3-dichloro-l-propanol [616-23-9]. The 1,1-addition of chloroform [67-66-3] as well as the addition of other polyhalogen compounds to vinyl chloride are cataly2ed by transition-metal complexes (58). In the presence of iron pentacarbonyl [13463-40-6] both bromoform [75-25-2] CHBr, and iodoform [75-47-8] CHl, add to vinyl chloride (59,60). Other useful products of vinyl chloride addition reactions include 2,2-di luoro-4-chloro-l,3-dioxolane [162970-83-4] (61), 2-chloro-l-propanol [78-89-7] (62), 2-chloropropionaldehyde [683-50-1] (63), 4-nitrophenyl-p,p-dichloroethyl ketone [31689-13-1] (64), and p,p-dichloroethyl phenyl sulfone [3123-10-2] (65). 

Phenazine reacts with benzenesulphinic acid in alcoholic hydrogen chloride to give 2-phenazinyl phenyl sulfone (26 Scheme 4), presumably by an intermediate 5,10-dihy-drophenazine this reaction is evidently a useful method of preparing 2-substituted phenazines, since the sulfone is readily displaced in substitution reactions. 

Novolacs are usually made under acidic conditions. Oxalic, sulfuric, toluene sulfonic, phenyl sulfonic, methane sulfonic, hydrochloric, and phosphoric acids are the most common catalysts, though nearly any moderately strong acid will probably do. Often selection of the acid has significant effects on the resultant polymer structure or performance. Sometimes acids are selected for their volatility, as it may be necessary to distill the acid off in some processes. 

Convenient syntheses of vinyl fluorides are of synthetic interest, fhe conjugate base of fluoromethyl phenyl sulfone reacts with carbonyl compounds to provide P-tluoro alcohols, which are used to prepare terminal vinyl fluorides [25] (equation 23) (Table 9) This reaction offers an alternative to the Winig reaction, which may be very sensitive to reaction conditions. 

Tetrahydropyranyl phenyl sulfone, MgBr2-Et20, NaHC03, THF, rt, 47-99% yield. ... 

In conclusion, all results obtained thus far on this reaetion show that it is espeeially the 4-position in the 3-nitro-l,8-naphthyridines whieh is strongly favored toward the attaek of the earbanion of ehloromethyl phenyl sulfone. When position 4 is oeeupied by a substituent no reaetion oeeurs. Tliis behavior is in aeeordanee with the behavior observed in reaetions with liquid ammonia and liquid methylamine. 

Also, the observed highly regioselective course in the SnFI substitutions in 2-R-3-nitro-l, 8-naphthyridines (R = FI, OFI, Cl, NFI2, OEt) with the anion of chloromethyl phenyl sulfone was explained by MNDO quantum-chemical calculations showing that, like in the aminations, the interaction of FIOMO of the nucleophile with LUMO of the nitronaphthyridines controls the regioselectivity (91JFIC1075). 

The reaction of 3-methoxy-1,2,4-triazine 1-oxide 20 with the carbanion generated from chloromethyl phenyl sulfone proceeds as the vicarious nucleophilic substitution (VNS) of hydrogen (Scheme 1, path B) via addition of the carbanion at position 5 of the heterocycle. Following base-induced elimination of HCl and protonation, 3-methoxy-5-phenylsulfonyl-1,2,4-triazine 4-oxides 65 result (88LA627). 

At the same time, the reaction of 1,2,4-triazine 4-oxides 55 with the anion of chloromethyl phenyl sulfone affords 5-(l-chloro-l-phenylmethyl)-l,2,4-triazines 66. In this case, autoaromatization of the a -adducts proceeds by the deoxygenative... 

Carbanions of ct-chloroalkyl phenyl sulfones react with nitrobenzenes to effect tlirect nucleophilic replacement of hydrogens located on o and para to the nitro group fEq. 9.24. A very important feature is that VNS of hydrogen usually proceeds faster than conventional SnAt of halogen located In equally activated positions fEq. 9.25. The rule that VNS of... 

Control of the regioselecdvity of VNS is important. It is governed by three major factors the stnicture of the nitroarene the nature of the nucleophile, and the reacdon condidons, especially solvent and base. The different effect of methoxy and hydroxy groups is interesdng the reacdon of Tmethoxy-2,4-dinitrobenzene vdth cbloromethyl phenyl sulfone proceeds in... 

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)... 

C7H802S, Methyl phenyl sulfone [(Methylsulfonyl)benzene]... 

C9H802S, (1 -Propynylsulfonyl)benzene C9H802S, (2-Propynylsulfonyl)benzene C9H802S, Allenyl phenyl sulfone [(l,2-Propadienylsulfonyl)benzene]... 

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. 

Dimetal derivatives 283 of alkyl and benzyl phenyl sulfones were found to react with aldehydes or ketones to give a, /J-unsaturated phenyl sulfones 284 in good yields366. 

In the condensation reaction between chloro- and bromo-methyl aryl sulfones and carbonyl compounds, a-sulfonyloxiranes were obtained. In this condensation reaction, bases such as potassium t-butoxides372, NaH373 and aqueous concentrated hydroxide with benzyltriethylammonium chloride under two-phase condensation were used374. In the reaction with aldehydes only the trans-epoxide isomers resulted, whereas lith-iofluoromethyl phenyl sulfone 289375 and 291376 were found to add to aldehydes affording /J-hydroxysulfones 290 and 292, respectively. 

The lithio-derivative derived from cyclohexyl phenyl sulfone underwent 1,2-addition to cyclohexenylideneacetaldehyde or cinnamaldehyde to give the corresponding / -hydroxysulfones387. Reactions of 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide 308... 

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