Diphenyl sulfone-3,3 -disulfonyl chloride

The cyclization of diphenyl ether 206 to the cyclic sulfone derivatives 208 and 209 achieved by prolonged heating with a large excess of the reagent is analogous to similar reactions observed with biphenyl and the diphenyl alkanes (see Section 2, pp 42 and 40). 4-Bromodiphenyl ether by treatment with excess chlorosulfonic acid (two equivalents) at 25-30 °C afforded the 4-sulfonyl chloride (45%). In this molecule, the other reactive 4-position is blocked by the bromine atom. In contrast, with diphenyl ether 206 all attempts to obtain the monosulfonyl chloride by reaction with chlorosulfonic acid failed, and the only isolated product was the 4,4 -disulfonyl chloride. In the case of 4,4 -dibromodiphenyl ether, in which... 

It was also discovered that diphenyl sulfone 223, by prolonged heating with chlorosulfonic acid (six equivalents) at 90 °C, gave a low yield of the 3-sulfonyl chloride 225 (Equation 71). Treatment of ethyl phenylsulfone and its p-chloro derivative with the reagent both yield the corresponding 3-sulfonyl chlorides so that sulfonation occurs, as expected, in the meta position relative to the sulfonyl group. Di-p-xylylsulfone reacts with chlorosulfonic acid (10 parts, 150-160 °C) to yield the 3,3 -disulfonyl chloride. ... 

These sulfone polymers e.g. 53) may also be prepared by polysulfonation of diphenyl ether 54 with the corresponding 4,4 -disulfonyl chloride 55 (Equation 7). 

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