Science of Synthesis

Suffert, J., Science of Synthesis, (2005) 26, 939.

The oxidation of ketones by thallium salts can be performed in acidic conditions with thallium(III) sulfate,[‌189‌] or under neutral conditions with thallium(III) 4-toluenesulfonate.[‌190‌] In both cases enolization is a prerequisite for attack by the thallium salt, although there are subtle differences in the way the metal is finally displaced. In acid this is achieved by the solvent acting as a nucleophile, whereas under neutral conditions the enol tautomer of a ketone ‌217‌ is converted into a metalated intermediate ‌218‌. A 4-tolu­enesulfonate anion is then responsible for cleaving the weak Tl—C bond to release the α-tosyloxy ketone ‌219‌ (‌Scheme 100‌).

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References

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• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) 8/8e8, 888.