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Identification of Adducts Formed in the Reaction of the Bacterial Mutagen 3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone with Cytidine

Pluskota-Karwatka D., Munter T., Le Curieux F., Sjöholm R., Koroniak H., Kronberg L.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

1145-1157

3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF), a strong bacterial mutagen reacts with cytidine in buffered aqueous solutions. The reaction products were separated by preparative HPLC C18 column chromatography and were structurally characterized by UV absorbance, 1H NMR and 13C NMR spectroscopy, and mass spectrometry. The main products were identified as 7-(-D-ribofuranosyl)-4-carboxy-6- oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (cM1FA-Cyd), and 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (M1FA-Cyd). The highest yields of cM1FA-Cyd andM1FA-Cyd, being 12 and 1mol%respectively, were obtained in the reaction performed at pH 4.6 and 37 graduateC for 7 days. M1FA-Cyd and cM1FA-Cyd are structurally related to pfA-dR, the adduct previously identified in the reaction of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) or 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF) with 2'-deoxyadenosine.

New application of 1,1,3,3,3-Pentafluoropropene-diethylamine Adduct (PFPDEA) as Fluorinating Agent. Synthesis of 3,3,3-Trifluoropropionates of Vicinal Fluorohydrins

Walkowiak J., Haufe G., Koroniak H.

Polish Journal of Chemistry

2004

Vol. 78 / nr 9

1777-1784

Reaction of various omega-fluoro-(omega-1)-hydroxy and omega-hydroxy-(omega-1)-fluoro fatty acid methyl esters with adduct of 1,1,3,3,3-pentafluoropropene-diethylamine (PFPDEA) has been studied. As a products mixture of corresponding vicinal difluorides and vicinal fluoro-3,3,3-trifluoropropionates was obtained.

The Influence of Fluorine Substitution on Diels-Alder Reaction of 3-Vinylcoumarin and Ethylene

Koroniak H., Pasikowska M., Fiedorow P.

Polish Journal of Chemistry

2003

Vol. 77 / nr 11

1523-1528

Density Functional Theory (DFT) has been applied to study the concerted mechanism of the Diels-Alder reaction between 3-vinylcoumarin and ethylene, as well as their fluorinated analogues. The main goal was to establish the fluorine influence on reactivity and structure of transition state (TS) and predict the reaction path. Computations were performed at the B3LYP/6-31G* level, which allowed to optimise the structure of reactants and products.