CHLOROSULFONATION OF SOME COMPOUNDS CONTAINING 2 PHENYL RINGS

Diphenylmethane (1) and dibenzyl (17) reacted with chlorosulphonic acid to give the corresponding p, p'-disulphonyl chlorides (2, 18). However, attempted chlorosulfonations of α-chloro-, αα'dichlorodiphenylmethane, stilbene and 1, 4-diphenylbutadiene were unsuccessful. Diphenylacetic acid reacted with chlorosulfonic acid to give a mixture of 4, 4'-dichlorosulfonylbenzophenone (40) and αchlorodiphenylmethane-4, 4'-disulfonyl chloride (39). Benzilic acid (41) afforded 9-chlorofluorene-2, 7-disulfonyl chloride (42), which with amines gave 3 different products according to the reaction conditions. Fluorene (53) and the 9-carboxylic acid (43) have been treated with chlorosulfonic acid. The various sulfonyl chlorides were converted into 43 derivatives for biocidal evaluation. Mechanistic interpretations for the reactions are included. © 1990, Taylor & Francis Group, LLC. All rights reserved.