Five of the title N-oxides 1 when reduced either chemically (phenylhydrazine, hydrazobenzene) or electrochemically (DMF-TEAP-protonating agent) were found to afford the corresponding 5- hydroxyindoles 6. The reduction process takes place in two steps leading initially to 1.5- dihydroxyindoles 4 which undergo loss of water and are eventually converted into the products. EPR spectroscopic studies of the chemical and electrochemical reduction led to the characterization of the intermediate radical anions and neutral radicals, and a mechanism based on these results as well as on polarographic and cyclic voltammetric studies is proposed for the process.
Chemical and electrochemical reduction of 2H-indole-3,5-dione and -dione 3-imine N-oxides / Carloni, Patricia; Damiani, Elisabetta; Greci, L.; Stipa, Pierluigi; Alberti, A.; Benaglia, M.; Marrosu, G.; Trazza, R. PETRUCCI E. A.. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - (1993), pp. 2217-2222. [10.1039/P29930002217]
Chemical and electrochemical reduction of 2H-indole-3,5-dione and -dione 3-imine N-oxides.
CARLONI, PATRICIA;DAMIANI, Elisabetta;L. GRECI;STIPA, Pierluigi;
1993-01-01
Abstract
Five of the title N-oxides 1 when reduced either chemically (phenylhydrazine, hydrazobenzene) or electrochemically (DMF-TEAP-protonating agent) were found to afford the corresponding 5- hydroxyindoles 6. The reduction process takes place in two steps leading initially to 1.5- dihydroxyindoles 4 which undergo loss of water and are eventually converted into the products. EPR spectroscopic studies of the chemical and electrochemical reduction led to the characterization of the intermediate radical anions and neutral radicals, and a mechanism based on these results as well as on polarographic and cyclic voltammetric studies is proposed for the process.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
