The Journal of Organic Chemistry

Thermal and photochemical nitration of aromatic hydrocarbons with nitrogen dioxide

E Bosch, JK Kochi

Index: Bosch, E.; Kochi, J. K. Journal of Organic Chemistry, 1994 , vol. 59, # 12 p. 3314 - 3325

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Citation Number: 72

Abstract

Aromatic hydrocarbons (ArH) are readily nitrated by nitrogen dioxide (Nod in dichloromethane at room temperature and below (in the dark). The red colors, transiently observed, arise from the metastable precursor complex [ArH, NO+ lN03-, which is formed in the prior disproportionation of nitrogen dioxide induced by the aromatic donor (eq 7). The deliberate irradiation of the diagnostic (red) charge-transfer absorption band (hvm) of [ArH ...