Kinetic investigations show that whereas 2,4- and 2,5-dialkylthiazoles undergo nitration as their protonated forms at all acidities studied, 2-thiazolones are nitrated via a free base mechanism at least at the lower acidities. The reactivities are discussed in terms of standard rates extrapolated to 25° and Ho–6.6.
A. R. Katritzky, C. Ögretir, H. O. Tarhan, H. M. Dou and J. V. Metzger, J. Chem. Soc., Perkin Trans. 2, 1975, 1614 DOI: 10.1039/P29750001614
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