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Landais, Y.; Vincent, J. M., Science of Synthesis, (2005) 26, 667.
Hydrolysis of α-oxo ketals (Section 26.4.1.1.2.1), α-oxo imines (Section 26.4.1.1.2.3), and α-oxo thioketals (Section 26.4.1.1.2.2) follows the same trends as observed for the simple ketal, imine, or thioketal compounds. α-Oxo ketals are easily hydrolyzed under mildly acidic conditions while the corresponding α-oxo thioketals are more stable and thus require harsher conditions such as the use of a heavy metal (mercury) or oxidative conditions. α-Oxo imines are hydrolyzed using acidic or oxidative conditions. α-Diazo ketones (Section 26.4.1.1.2.5) react selectively with oxidants such as potassium peroxymonosulfate (Oxone) or peracids to give di- and triketones in excellent yields. Finally, α,α-dihalo ketones (Section 26.4.1.1.2.4) appear to be less stable and are quite sensitive to hydrolysis, reacting with mild reagents such as sodium acetate.
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