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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.

Synthesis of (R) and (S) 2-phenoxypropionamide derivatives as new compounds with promising pesticidal activity

Ochal Z., Gajadhur A.

Polish Journal of Applied Chemistry

2004

Vol. 48, nr 1-2

33-44

The synthesis of (R) and (S) 2-phenoxypropionamide derivatives as new compounds with potential pesticidal activity is reported. The title compounds were obtained by the three - step synthesis starting from (R) and (S) 2-phenoxypropionic acid ethyl esters. Esters were hydrolyzed, and obtained acids were converted into chlorides applying the thionyl chloride. Phenoxy acid chlorides were subjected to the reaction with amines, to give the title compounds. Optical purity of the synthesized compounds were determined using HPLC equipped with chiral columns. Characteristic IR spectroscopic data and the results ofmicroelemental analyses of the new products are given.

Przedstawiono syntezę nowych pochodnych (R) i (S) 2-fenoksypropionamidu jako związków o spodziewanej aktywności pestycydowej. Związki te otrzymywano w trójetapowej syntezie, wychodząc z estrów etylowych kwasu (R) i (S) 2-fenoksypropionowego. Estry te hydrolizowano, a otrzymane kwasy przekształcano w chlorki kwasowe stosując chlorek tionylu. Chlorki fenoksykwasów poddano reakcji z aminami uzyskując tytułowe pochodne. Czystość optyczną syntezowanych związków określano metodą HPLC stosując chiralne kolumny. Podano charakterystyczne pasma IR oraz wartości analizy elementarnej otrzymanych nowych pochodnych.