”Radical anions containing the dioxidated 1,2,5-thiadiazole heterocycle”.

MARıA VIRGINIA MIRıFICO; JOSE ALBERTO CARAM; ANA MARıA GENNARO; CARLOS J. COBOS; ENRIQUE JULIO VASINI

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

John Wiley & Sons, Ltd

Lugar: Chichester, England; Año: 2008

0894-3230

Radical anions of 3,4-aryl disubstituted 1,2,5-thiadiazole 1,1-dioxide have been 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 C-N bond of the thiadiazoles. A possible reaction mechanism, and a common reaction intermediate, supported by density functionaltheory calculations, is presented for the most stable radical.