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Please login to access the full content or check if you have access via Variation 6: By Oxidation with Thallium(III) Salts

DOI: 10.1055/sos-SD-026-00761

Suffert, J.Science of Synthesis, (200526939.

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 TlC bond to release the α-tosyloxy ketone 219 (Scheme 100).

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