Abstract: The 0-deuterated enolic tautomers 3-deuteroxybenzofuran, 3- deuteroxybenzothiophene, 3-deuteroxyindole, 3-deuteroxy-1-methylindole, 3- deuteroxyfuran, 3-deuteroxythiophene, 2-deuteroxybenzothiophene, and 2- deuteroxythiophene have been generated in solution in mixtures of CD3COCD3, CD3CN, or CD3SOCD3 with D20 by hydrolysis of their trimethylsilyl derivatives in the presence of DCI ...