STUDIES ON THE DEUTERATION OF AROMATIC ORGANOSULFUR COMPOUNDS USING AQUEOUS TRANSITION METAL SPECIES

Autor:	Alex Primak, Peter D. Clark
Rok vydání:	1993
Předmět:	Aqueous solution Bicyclic molecule Organic Chemistry Inorganic chemistry Biochemistry Medicinal chemistry Inorganic Chemistry Metal Electrophilic substitution chemistry.chemical_compound chemistry Transition metal visual_art Electrophile visual_art.visual_art_medium Thiophene Organosulfur compounds
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 84:149-157
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426509308034326
Popis:	Reaction of benzenethiols and benzo[b]thiophene (BT) with D2O solutions of trichlorides of Ru, Fe or Cr at elevated temperatures (200–315°C) constitutes a simple method for the preparation of per-deuterated derivatives. Substitution patterns observed for partially deuterated products imply that D-incorporation occurs by standard electrophilic processes. 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 transition metal 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.
Databáze:	OpenAIRE
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