Electrosynthesis of 3-Nitrophenotiazine. Nitration in Non-Aqueous Solutions.docVIP

374 Molecules 2000, 5 Electrosynthesis of 3-Nitrophenotiazine. Nitration in Non-Aqueous Solutions P.A. Perlo, M.N. Cortona, J.J. Silber and L.E. Sereno Dpto de Química y Física, Universidad Nacional de Río Cuarto. Agencia Postal N: 3, 5800, Río Cuarto, Argentina E-mail: pperlo@.ar Abstract: The nitration of Phenothiazine (PHEN) in acetonitrile (ACN) in the presence of excess NaNO2 has been studied in detail. First, the electrochemical behavior of the reactants was investigated by cyclic voltammetry to determine the electrolysis conditions. Controlled- potential electrolysis was used for the electrosynthesis. Introduction Although the nitration of organic compounds is an area in expansion since the beginning of the century principles, its interest has not diminished. In this way, new nitration methods that outline new challenges for the interpretation of the mechanisms have appeared. The principal interest resides in that the nitrated products are fundamental source of diverse synthetic products [1-3]. The traditional nitra- tion methods, which use aggressive mixtures of nitric and sulfuric acid, are being left, due to the high cost of the effluents treatment [4]. The electrochemical methods are an excellent way to produce the nitration intermediates [5]. Besides, it constitutes an interesting alternative procedure from the mecha- nistic point of view. Experimental An EG PAR model 273 potensiostat-galvanostat was used for cyclic voltammetry (CV) and con- trolled-potential electrolysis (CPE) measurements, using a conventional three-compartment Pyrex cell, stirring with a Teflon paddle for the EPC. The working electrodes were Pt wires of area 0.235 cm2 for CV, and Pt electrodes of larger area (ca.16 cm2) for CPE. The counter-electrode was a stainless steel foil of large area. All the potentials were referred to a saturated calomel electrode (SCE) and were cor- rected for IR drop by positive feedback techniques. The