Some Phenoxybenzenesulfonyl Chlorides and Related Compounds

Abstract

Phenoxybenzene (diphenyl ether) has been converted into the 4-sulfonyl chloride (1) which on condensation with various nucleophilic reagents gave a range of sulfonyl derivatives (2-11), such as the azide, hydrazides, and hydrazones. The sulfonyl chloride (1), by nitration, gave 4-(4'-nitrophenoxy)benzenesulfonyl chloride (12) which was similarly converted into sulfonyl derivatives (13-18).

Reaction of o-chlorophenol with p-chloronitrobenzene afforded 2-chlorophenyl 4-nitrophenyl ether; with chlorosulfonic acid this gave the sulfonyl chloride (19) which was converted into the sulfonyl derivatives (20)-(25). Condensation of 2,6-dichlorophenol with p-chloronitrobenzene similarly gave the substituted diphenyl ether (26) which with chlorosulfonic acid afforded 3,5- dichloro-4-(4'-nitrophenoxy)benzenesulfonyl chloride (27). The phenoxybenzenesulfonyl derivatives are of interest as potential herbicides and their algicidal and antibacterial properties are briefly discussed.