119408-14-9Relevant articles and documents
FORMATION OF METHOXY-SUBSTITUTED AZOXYBENZENES IN THE REDUCTION OF NITROARENES IN BASIC METHANOL-TOLUENE SOLUTIONS
Prato, Maurizio,Quintily, Ugo,Scorrano, Gianfranco
, p. 421 - 426 (2007/10/02)
The reduction of nitroarenes in boiling methanol-toluene containing KOH affords high yields of the corresponding azoxy derivative and small amounts of other azoxy compounds containing one or more OCH3 groups linked to the aromatic rings.It has been proved that the reaction does not occur via formation of methoxy-nitroarenes and their further reduction.The reaction is proposed to involve: a) formation of a Meisenheimer complex by attack of the methoxide ion on the nitroarene; b) abstraction of a proton from the Meisenheimer complex by a methoxide ion to form a dianion; c) protonation of the dianion with concurrent elimination of OH to form the nitroso-methoxy arene which is finally reduced to the methoxy-azoxy derivative.It is proposed that the dianion is the electron-donating species to start the reduction of nitro- and nitrosoarenes.