Spectroscopic Evidence for a Spirooxirane Intermediate in the Synthesis of 4-(Hydroxymethyl)-2-thiazole

Article abstract of DOI:10.1021/jo00036a022

The synthesis of 4-(hydroxymethyl)thiazole derivatives from the corresponding 4-(chloromethyl)-4-hydroxythiazole derivatives have been speculated to proceed through spirooxirane intermediates.NMR spectroscopy was used to provide evidence for the existence of such an intermediate in the synthesis of 4-(hydroxymethyl)-2-<(dimethylamino)methyl>thiazole.Experimental conditions for the optimum formation and stabilization of a suspect intermediate were determined and spectral data obtained to support the speculated structure.Comparison were made between couplings constants predicted in molecular models and the experimental data.