Whereas isothiazole and its 3- and 5-methyl derivatives are all nitrated solely as free bases, the 3,5-dimethyl analogue shows a mechanistic changeover to nitration as conjugate acid. The effects of methyl groups on the reactivity are discussed in comparison with hydrogen exchange.
A. R. Katritzky, H. O. Tarhan and B. Terem, J. Chem. Soc., Perkin Trans. 2, 1975, 1620 DOI: 10.1039/P29750001620
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