The dichotomy between nitration of substituted 1,4-dimethoxybenzenes and formation of corresponding 1,4-benzoquinones by using nitric and sulfuric acid †
Free accessOtherFirst published online March, 2000
The dichotomy between nitration of substituted 1,4-dimethoxybenzenes and formation of corresponding 1,4-benzoquinones by using nitric and sulfuric acid †
Various alkyl-substituted p-dimethoxybenzenes (ArH) react readily with nitric acid and sulfuric to form nitro-products (ArNO2). When the nitric acid is used in excess, the nitro-product react via either nitration to dinitro-compound (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.
References
1.
(a) SchofieldK., Aromatic Nitration, Cambridge University Press, Cambridge1980
2.
OlahG.A., MalhotraR., NarangS. C., Nitration: Methods and Mechanisms, VCH, New York, 1989.
3.
(a) HabermannJ., Chem. Ber., 1978, 11, 1034
4.
MoureuM. Ch., Bull. Soc. Chim. Fr., 1986, 646.
5.
(a) SankararamanS., HaneyW. A., KochiJ. K., J. Am. Chem. Soc., 1987, 109, 5235
6.
KimE.K., LeeK. Y, KochiJ. K., J. Am. Chem. Soc., 1992, 114, 1756
7.
YabeT., KochiJ. K., J. Am. Chem. Soc., 1992, 114, 4491
8.
KimE.K., BockmanT. M., KochiJ. K., J. Am. Chem. Soc., 1993, 115, 3091.
