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

MARÍA VIRGINIA MIRÍFICO*; JOSÉ ALBERTO CARAM; CARLOS JORGE COBOS; ANA MARÍA GENNARO; ENRIQUE JULIO VASINI

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

John Wiley & Sons, Ltd.

Lugar: Chichester. England; Año: 2009 vol. 22 p. 964 - 970

0894-3230

Radical anions of 3,4-aryl disubstituted 1,2,5-thiadiazole 1,1-dioxide have been obtained by chemical and by 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 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 functional theory calculations is presented for the most stable radical.