Producción CyT
Radical anions containing the dioxidated 1,2,5-thiadiazole heterocycle

Artículo

Autoría
María Virginia Mirífico ; José Alberto Caram ; Ana María Gennaro ; COBOS, CARLOS JORGE ; Enrique juio Vasini
Fecha
2008
Editorial y Lugar de Edición
JOHN WILEY & SONS LTD
Revista
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, vol. 22 (pp. 964-970) JOHN WILEY & SONS LTD
Resumen Información suministrada por el agente en SIGEVA
Radical anions of 3,4-aryl disubstituted 1,2,5-thiadiazole 1,1-dioxide were obtained by chemical and electrochemical reduction of their substrates, and characterized by ESR spectroscopy and cyclic voltammetry. The radical anion of the phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxide was found to be very stable in an aprotic solvent solution and did not react readily when water was added to the aprotic solvent, or the solution was saturated with oxygen gas. The radical formation chemical reactio... Radical anions of 3,4-aryl disubstituted 1,2,5-thiadiazole 1,1-dioxide were obtained by chemical and electrochemical reduction of their substrates, and characterized by ESR spectroscopy and cyclic voltammetry. The radical anion of the phenanthro[9,10-c]-1,2,5-thiadiazole 1,1-dioxide was found to be very stable in an aprotic solvent solution and did not react readily when water was added to the aprotic solvent, or the solution was saturated with oxygen gas. The radical formation chemical reaction competed with nucleophilic addition to the CN bond of the thiadiazoles. A possible reaction mechanism, and a common reaction intermediate, supported by density functional theory calculations, is presented for the most stable radical
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Palabras Clave
Organic electrochemistryEPR spectroscopyThiadiazolRadical anionDFT calculation