Phenol-2,4-disulfonyl chloride

Hydroxybenzene-13-disuironyl chloride (Phenol-2,4 disulfonyl chloride)... 

Various synthetic approaches have been demonstrated for the synthesis of PAEs since early days [35 0], PAEs were synthesized by Ullmann condensation between bisphenols and aryl fcis-halide monomers using Cu(I) salt/pyridine as catalyst [36], General Electric developed the first commercially successful PAE poly(2,6-dimethyl phenylene oxide) (PPO) [38], It was prepared by oxidative coupling of 2,6-dimethyI phenol. However, this process has its own restrictions, because it does not allow much structural variation or inclusion of any electron-withdrawing group into the polymer main chain. First attempts to synthesize polysulfones (PSF) were successfully done by Friedel-Crafts sulfonylation reaction of arylenedisulfonyl chlorides, for example, diphenyl ether-4,4 -disulfonyl chloride with diaryl ethers, for example, diphenyl ether, or by self-condensation of 4-phenoxy benzene sulfonyl chloride in the presence of FeCls [41], Whereas the former reaction involves side reactions (sulfonylation not only in the para- but also in the ort/io-position), the latter produces only the desired linear all-para products. 

Phenol 116, by treatment with excess chlorosulfonic acid, yields the 2,4-disulfonyl chloride and heating the substrate with a large excess of the reagent at 130-140 °C (4-5 hours) affords the 2,4,6-trisulfonyl chloride, but no sulfony-lide derivative was reported from this substrate. 

The action of chlorosulfonic acid on di- and polyhydric phenols has been examined. Catechol (1,2-dihydroxybenzene, 151) reacts with the reagent (two equivalents) at room temperature (24 hours) to yield the 3,5-disulfonic acid 152. On the other hand, heating catechol 151 with excess reagent (10 equivalents) at 110°C afforded the corresponding disulfonyl chloride 153 (Equation 50). If the reaction mixture is heated at 150 °C (8 hours), the product was the cyclic sulfate of the 3,5-disulfonyl chloride 154 (Equation 50) which is probably formed by acid-catalysed dehydration of the initially formed hydrogen sulfate 155. ... 

Alkyl phenols, e.g. cresols and xylenols, by heating with a large excess of chlorosulfonic acid (10 equivalents), are sulfonated and cyclized to the corresponding sulfonylide disulfonyl chlorides. Thus o-cresol yields the cyclized product 7 and a similar reaction was also observed with 8-acetyl-7-hydroxy-4-methylcoumarin (see Chapter 6, p 202). 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ ]

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