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CONTROLLED chlorosulponation of diphenylsulphone (1), thiaxanthone (2) and benzophenone (3) with chlorosulphonic acid yielded diphenylsulphone-3,3′- disulphonyl-chloride (4a), thiaxanthone-3,3′- disulphonylchloride (5) and benzophenone -3,3′-di

-Sulfonation of substituted diphenyl sulfones with excess chlorosulfonic acid at 100°C yields as a rule the corresponding bis-sulfonyl chlorides. The reaction with an equimolar amount of 20% oleum yields products of sulfonation of only one benzene ring.

Benzophenone (1), diphenyl sulfone, and 4-nitro-2'-chloro- and 4-nitro-2',6'-dichlorophenyl ethers (23,24) have been chlorosulfonated.The direct yield of benzophenone-3,3'-disulfonyl chloride (2) was low, the majority of product was the disulfonic acid.Diphenyl sulfone (11) with a large amount of chlorosulfonic acid (8 mols) at 140 deg gave the 3,3'-disulfonyl chloride (12).With less reagent (6 mols) at 90 deg a mixture of the 3-sulfonyl chloride (21) and diphenyl sulfone was formed.Subsequent reaction with sodium azide gave the 3-sulfonyl azide (22).The diphenyl ether sulfonyl chlorides (25,26) were very susceptible to hydrolysis, especially (26) which probably accounts for the low yield obtained (31percent).The various sulfonyl chlorides were characterized as amides, azides, hydrazides and hydrazones (Tables I-III) and their i.r., n.m.r., and mass spectral data are included.

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