RSC Publishing


Publishing

 

Cover image for Perkin Transactions 2, click here for current issue

Perkin Transactions 2

Perkin Transactions 2 ceased publication in 2002. Organic & Biomolecular Chemistry is the RSC's organic chemistry journal for high-quality, original organic chemistry research.



Journals archive purchasers

Non-journals archive purchasers

Free access



Paper

J. Chem. Soc., Perkin Trans. 2, 1993, 2217 - 2222, DOI: 10.1039/P29930002217

Chemical and electrochemical reduction of 2H-indole-3,5-dione and -dione 3-imine N-oxides

Patricia Carloni, Elisabetta Damiani, Lucedio Greci, Pierluigi Stipa, Angelo Albert, Massimo Benaglia, Giancarlo Marrosu, Rita Petrucci and Antonio Trazza

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.