Journal of the Chemical Society. Perkin transactions II p. 813 - 818 (1982)
Update date:2022-08-25
Topics:
Penn, David
Satchell, Derek P. N.
The kinetics of the mercury(II) ion-promoted hydrolysis of 2-phenyl-1,3-oxathiolan (1) have been studied at various pH values and ambient chloride ion concetrations using dioxan-water and ethanol-water solvents.The products are always benzaldehyde and 2-mercaptoethanol.In the absence of mercury(II) ions the hydrolyses are comparatively slow.Hg2+ and (1) rapidly form a 1:1 adduct (2) in solution with a formation constant K ca. 1.8x103 at 25 deg C.Depending upon the pH, either (2) or its protonated or deprotonated form reacts to give a hemiacetal whose subsequent hydrolysis is fast.The ring-opening process may involve intramolecular transfer of mercury-bond aquo species.In ethanol-water solvents (2) also reacts with ethanol to give a (small) quantity of an open-chain OO-acetal (3) whose subsequent hydrolysis is relatively slow.Added chloride ions reduce the competition from this ethanol reaction but also catalyse the hydrolysis of (3).Chloride ions have complex effects on the rate of the direct hydrolysis of (1)
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