The ortho–para-isomer ratios of the nitration products can be reversed from ortho-rich (o/p= 1.10 and 1.09) to para-predominant (o/p= 0.45 and 0.68) simply by altering the initial concentration of the substrate in the ozone-mediated reaction of chloro- and bromo-benzenes with nitrogen dioxide.
H. Suzuki, T. Mori and K. Maeda, J. Chem. Soc., Chem. Commun., 1993, 1335 DOI: 10.1039/C39930001335
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