91013-42-2Relevant academic research and scientific papers
The dichotomy between nitration of substituted 1,4-dimethoxybenzenes and formation of corresponding 1,4-benzoquinones by using nitric and sulfuric acid
Waterlot,Haskiak,Couturier
, p. 106 - 107 (2007/10/03)
Various alkyl-substituted p-dimethoxybenzenes (ArH) react readily With nitric acid and sulfuric to form nitroproducts (ARNO2). When the nitric acid is used in excess, the nitro-product react via either nitration to dinitrocompound (Ar(NO2)2) or via oxidative demethylation to nitro-p- quinone (Q). As such, the competition between the nitration, polynitration and oxidative dealkylation is effectively modulated by the added nitric acid and the alkyl-substituted p-dimethoxybenzenes.
Selective nitration versus oxidative dealkylation of hydroquinone ethers with nitrogen dioxide
Rathore,Bosch,Kochi
, p. 6727 - 6758 (2007/10/02)
Various alkyl-substituted p-dialkoxybenzenes (ArH) react readily with nitrogen dioxide (NO2) in dichloromethane solution via either nitration (ArNO2) or oxidative dealkylation to quinones (Q). Spectral transients indicate that these coupled processes proceed from the dialkoxybenzene radical cation (ArH+) formed as the common reactive intermediate from electron-transfer in the disproportionated precursor [ArH, NO+]NO3-. In fast subsequent steps, ArH+ undergoes homolytic coupling with NO2 (which leads to aromatic nitration) and nucleophilic attack of NO3- (which results in oxidative dealkylation). As such, the competition between nitration and oxidative dealkylation is effectively modulated by solvent polarity and added nitrate.
