The kinetics and mechanism of the electrophilic substitution of heteroaromatic compounds. Part XLII. The nitration of thiazoles and thiazolones

Abstract

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.