The hydrolysis of six-membered ring acetals is faster than that of five-membered ring acetals. acetal and imine formation) or effect a reduction (e.g. Chemistry. Kinetic reaction scheme for hydrolysis of acetals and thioacetals of benzaldehyde. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry. Synthetic Communications: Vol. If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked.

Recent Literature. Selective Hydrolysis of Thioacetals with Thallium(III) Nitrate.

2036 Main Mall. Substituent effects, activation parameters, acidity dependencies and solvent isotope effects suggest that the acid-catalysed hydrolysis of diethyl thioacetals of meta- and para-substituted benzaldehydes, and of acetophenone, proceed via an essentially A1 scheme. Sterically hindered carbonyl compounds were converted to the corresponding thioacetals in refluxing petroleum ether in good yields.

(1979).

4, pp.

Thioacetals have been traditionally converted into carbonyls by hydrolysis with heavy-metal reagents such as mercury(II) salts, or by oxidation, and these approaches were discussed in chapter 3.01.1.10 of <1995COFGT(3)1>. Journal of the American Chemical Society 1980, 102 (9) , 3062-3071. You can change or update your cookiesettings at any time. DOI: 10.1021/ja00529a032. The cyclic sulfonium cation undergoes ring opening, and after nucleophilic attack by water, a second Hg-S bond under ring closure is formed. A convenient procedure for the hydrolysis of thioacetals using silver oxide in aqueous methanol is described. H. Firouzabadi, N. Iranpoor, K. Amani, Synthesis, 2002, 59-60. $\ce{Hg^2+}$ has a high affintity to thiols and other sulfur functional groups, and therefore $\ce{HgCl2}$ forms a Lewis acid-base adduct with the dithiane. 1.6.4 Thioacetals An aldehyde or ketone can react with a thiol ( R SH) in HA to form a thioacetal Additionally, an aldehyde or ketone can react with a di-thiol ( HS R SH) with BF Thomas H. Fife, Theodore J. Przystas. TCI uses cookies to personalize and improve your user experience. Aldehydes and ketones were protected as their thioacetals in the presence of a catalytic amount of iodine. 9, No.

Substituent effects, activation parameters, acidity dependencies and solvent isotope effects suggest that the acid-catalysed hydrolysis of diethyl thioacetals of meta- and para-substituted benzaldehydes, and of acetophenone, proceed via an essentially A1 scheme.
by hypervalent iodine) then hydrolysis; (3)Hydrolysis using Hg(II).


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