Chlorophenyl 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. 

Selection of appropriate conditions to modify polymers is facilitated by preliminary studies with well designed model compounds. The work with model systems is critical when studying condensation polymers because the main chain linkages have proved to be remarkably labile under certain conditions. Condensation of 4-chlorophenyl phenyl sulfone with the disodium salt of blsphenol-A yields 2,2-bis[4 -(4"-phenylsulfonylphenoxyl)phenyl] propane, T, an excellent model for the poly(arylene ether sulfone) substrate. Conditions for quantitative bromination, nitration, chloro-methylation, and aminomethylation of the model compound were established. Comparable conditions were employed to modify the corresponding polymers. 

The second order nature of quaternization reactions in our system was confirmed by rate studies on model compounds. Although benzyl chloride is usually selected as the model for chloro-methylated polymers , we chose to synthesize a difunctional model that would be sensitive to neighboring group effects. Condensation of 4-chlorophenyl phenyl sulfone with the disodlum salt of bis-phenol-A yielded an excellent model for the polysulfone segment, Quantitative chloromethylation of with a chloromethyl methyl ether/ methyl acetate mixture in the presence of stannic chloride afforded the corresponding bischloromethyl adduct,... 

Oae and Khim measured the rates of hydrolysis of chlorophenyl phenyl sulfoxides and sulfones with hydroxide ion in aqueous DMSO at 158 °C. Both SOPh and S02Ph were found to activate the nucleophilic substitution from ortho- and para-positions, but the effect of SOjPh was considerably larger than that of SOPh. The results were interpreted in terms of 7t(pd) conjugation in the intermediate complexes. In a later paper it was shown that the introduction of a methyl group ortho to SOPh or S02Ph slightly retards the above and related reactions but this was attributed to the inductive effect of Me rather than steric inhibition of 7t(pd) conjugation (Section III.A.l). 

Sulfonyl-bis(2,6-dinitrophenol) in CA 5th Decennial Formula Index] [called Bis(3.5-dinitro -4-oxy-phenyl)-sulfon or 3.5.3 .5 -Tetranitro-4.4 -dioxy-diphenylsulfon in Ger], 0aS[(02N)2C6H2.0H]2 mw 430.27, N 13.02% very bitter-tasting straw-yel ndlsffrom boiling w), mp 257-258°(Ref 4) insol in most org solvs can be prepd by nitrating either bis(3-nitro-4-hydroxy-phenyl)-sulfone or bis(4-hydroxyphenyl)-sulfone and by hydrolyzing bis(3,5-dinitro-4-chlorophenyl) -sulfone(Refs 1 2). It forms salts which can be used in ignition compositions(Ref 3)... 

It was reported earher that the oxidation of a sulfoxide to a sulfone involves either an initial nucleophihc attack of the nucleophilic oxidant or an electrophihc attack by an electrophilic oxidant. It is noteworthy that the oxidation of p-tolyl methyl, phenyl methyl and p-chlorophenyl methyl sulfoxides to the sulfones using the sulfonylperoxy intermediate 51 appears to be electrophihc, namely the relative reactivity order was p-tolyl methyl > phenyl methyl > p-chlorophenyl methyl sulfoxide based on competitive oxidations. 

Dichlorodimethyltin. See Dimethyltin dichloride 2,2 -((3,3 -Dichloro (1,r-diphenylj-4,4 -diyl) bis (azo)) bis (3-oxo-N-phenyl) butanamide. See Diarylanilide yellow Dichlorodiphenylsilane. See Diphenyidichlorosilane 4,4 -Dichlorodiphenyl sulfide CAS 5181-10-2 Synonyms CDPS Properties Wh. cryst. m.p. 97-98 C Uses Intermediate for org. synthesis Manuf./Distrib. Sumitomo Seika 4,4 -Dichlorodiphenyl sulfone CAS 80-07-9 EINECS/ELINCS 201-247-9 Synonyms Bis (p-chlorophenyl) sulfone 4-Chloro-1-(4-chlorophenylsulfonyl) benzene p-Chlorophenyl sulfone DDS p,p -Dichlorodiphenyl sulfone Di (4-chlorophenyl) sulfone Di-(p-chlorophenyl) sulfone 1,1 -Sulfonylbis (4-chlorobenzene)... 

Anisole (methyl phenyl ether) is extremely reactive towards sulfonation due to the presence of the strongly electron-donating (-fM) methoxy group. It therefore reacts with chlorosulfonic acid (two equivalents) at 0 °C to give mainly p-methoxybenzenesulfonyl chloride. With chlorobenzene, the chlorine atom exerts a strong electron-withdrawing (-1 effect) so sulfonation will be rather less easy than for benzene. Treatment of chlorobenzene with chlorosulfonic acid (four equivalents) at 25 C (3 hours) afforded p-chlorobenzenesulfonyl chloride (84%) and di(/7-chlorophenyl sulfone) (6%)." Chlorobenzene with chlorosulfonic acid (six equivalents) at 150-160 °C (8 hours) gave the 2,4-disulfonyl chloride. 

From these biphenols, polymers 28 with these different substituents on the imide nitrogen have been synthesized by reaction of the monomers with activated dihalides. The N-phenyl substituted biphenol, for example, gives a poIy(ether sulfone) by reaction with bis(4-chlorophenyl sulfone) which has a Tg of 310 C which has outstanding thermooxidatve stability... 

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