Synthesis, spectroscopic and structural properties of novel substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones

The reaction of chloral with substituted anilines resulted in formation of the respective 2,2,2-trichloroethylidene anilines. Subsequent treatment of these imines in situ with thioglycolic acid produced a series of substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones, This synthetic route was interesting in light of several other possible intermediates which can be formed on reaction of chloral with amines. High resolution (300 MHz) ¹H and ¹³C magnetic resonance spectra and ab initio calculations gave insight into the conformation of the observed products.