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Synthesis and transformation of 4-difluoromethylsulfonyl-2-nitrophenylsulfenyl chloride into new compounds with promising pesticidal activity

Ochal Z., Trojanowska A.

Polish Journal of Applied Chemistry

2008

Vol. 52, nr 3-4

131-138

The synthesis of 4-difluoromethylsulfonyl-2-nitrophenylsulfenyl chloride and its transformation into new compounds with potential pesticidal activity is reported. The title compound was obtained by three step synthesis starting from 4-difluoromethylchlorophenyl sulfone. It was nitrated and then subjected to the SNAr reaction with sodium disulfide to give proper diphenyl disulfide which was chlorinated by chlorine. Obtained phenylsulfenyl chloride was transformed into sulfonamide derivatives by reactions with amines.

Synthesis of (R) and (S)-2-[4-(4'-difluoromethylsulfonyl-2'-nitrophenylamino)phenoxy]propionic acid derivatives as new pesticides

Ochal Z., Gałązka J.

Polish Journal of Applied Chemistry

2006

Vol. 50, nr 1-2

13-27

The synthesis of (R) and (S)-2-phenoxypropionie acid derivatives bearing difluoromethylsulfonyl-nitrophenyl group, such as: phcnoxypropionamides, phenoxypropionhydrazides, phenoxypro-pionhydrazones and phcnoxypropionsemicarbazides as a new compounds with potential pesticidal activity is reported. The title compounds were obtained starting from the proper phenol synthesized from difluoroniethyl-3-nitro-4-chlorophenyl sulfone and 4-aminophenole. Obtained phenol was transformed into optically active phenoxypropionic acid ethyl esters in reaction with (S)-(-)-tosy!oxy ethyl lactate and (R)-(+)-2-chloropropionic acid ethyl ester. They were hydrolyzed, and then obtained acids were converted into chlorides. Phenoxy acid chlorides were subjected to the reaction with amines. Phenoxypropionic acid ethyl esters are transformed in reaction with hydrazine hydrate into hydrazides, which were used to the reaction with aldehydes and isocyanates. Optical purity of the synthesized compounds were determined using HPLC equipped with chiral columns. Characteristic IR spectroscopic data and microelernentary analyses of the new products are reported.