Capon, Brian published the artcileTautomerism of the monohydroxy derivatives of five-membered oxygen, nitrogen and sulfur heterocycles, Application of Thiophen-3-ol, the publication is Journal of the American Chemical Society (1989), 111(14), 5346-56, database is CAplus.
The O-deuterated enolic tautomers 3-deuteroxybenzofuran, 3-deuteroxybenzothiophene, 3-deuteroxyindole, 3-deuteroxy-1-methylindole, 3-deuteroxyfuran, 3-deuteroxythiophene, 2-deuteroxybenzothiophene, and 2-deuteroxythiophene were generated in solution in mixtures of CD3COCD3, CD3CN, or CD3SOCD3 with D2O by hydrolysis of their trimethylsilyl derivatives in the presence of DCl (10-3-10-1 M) and characterized by 1H NMR spectroscopy. Solutions of 3-hydroxypyrrole and of 3-hydroxy-1-methylpyrrole were obtained by methanolysis of their trimethylsilyl derivatives, evaporation of the methanol, and immediate dissolution in DMSO-d6. The carbocyclic analogs of the bicyclic heterocyclic enols 3-deuteroxyindene and 2-deuteroxyindene were also generated in solution Attempts to prepare solutions of 2-deuteroxyfuran, 2-deuteroxypyrrole, and 2-deuteroxy-1-methylpyrrole were unsuccessful. The kinetics of ketonization of the OH forms of these enols were investigated in water or aqueous acetonitrile solution The equilibrium constants for the keto-enol tautomerism were also determined either by direct measurement when sufficient enol was present at equilibrium or as the ratio of the rate constant for enolization of the keto form to that for ketonization of the enol form, the former being determined by the iodine-trapping technique. The effect of solvent on the equilibrium constants was also studied. Sufficient data were available for the equilibrium between 3-hydroxyindole and 3-ketoindole for them to be analyzed by the four-parameter equation of Mills and Beak to yield an a-value of 2.4 and a b-value of -3.0. The pKas of the bicyclic enols were measured. 3-Hydroxybenzofuran and 3-hydroxybenzothiophene are stronger acids than 3-hydroxyindole and 3-hydroxy-1-methylindole. The ketonization reactions are general-acid and general-base catalyzed and their mechanisms are discussed.
Journal of the American Chemical Society published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Application of Thiophen-3-ol.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
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