84272-90-2Relevant academic research and scientific papers
STUDIES ON THE DEUTERATION OF AROMATIC ORGANOSULFUR COMPOUNDS USING AQUEOUS TRANSITION METAL SPECIES
Clark, Peter D.,Primak, Alex
, p. 149 - 158 (2007/10/02)
Reaction of benzenethiols and benzothiophene (BT) with D2O solutions of trichlorides of Ru, Fe or Cr at elevated temperatures (200-315 deg C) constitutes a simple method for the preparation of perdeuterated derivatives.Substitution patterns observed for partially deuterated products imply that D-incorporation occurs by standard electrophilic process.Reactions with benzenethiols produced diaryl sulfides as by-products although these compounds were deuterated to the same extent as the thiols.Experimental observations and the known behaviour of aqueous transitionmetal species indicate that D+ is furnished by the hydrolysis of D2O molecules in the solvation sphere of the metal ion.Complete deuteration of the organosulfur substrates was achieved using a 100:1 organosulfur/metal chloride mole ratio.Hydrodesulfurization of per-deuteroBT under standard conditions afforded perdeuteroethylbenzene in good yield.Key words: Aromatic organosulfur compounds; deuteration; aqueous transition metal salts.
