Synthesis of 4,5-dihydrothiazole derivatives by the reaction of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with ambident N,O- and N,S-nucleophiles

The reactions of perfluoro-2-methylpent-2-en-3-yl isothiocyanate with ambid ent N,O- and N,S-nucleophiles (thiazole-2-thione, pyridine-2-thione, 2-hydr oxypyridine, benzothiazole-2-thione, benzoxazole-2-thione, 3,4,5,6-tetrahyd ropyrimidine-2-thione) in the presence of triethylamine yield only 2-N-subs tituted 4,5-dihydrothiazole derivatives. The molecular structures of three products were determined by X-ray diffraction analysis, The reaction pathwa ys are discussed.