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21.1.5.8 Method 8: Willgerodt Reaction from Aryl Ketones

DOI: 10.1055/sos-SD-021-00115

Judd, W. R.; Katz, C. E.; Aubé, J.Science of Synthesis, (200521173.

The Willgerodt reaction involves the conversion of an aryl alkyl ketone, e.g. 119, into an amide, e.g. 120, containing the same number of carbons by heating with aqueous ammonium polysulfide. The terminal methyl group of the ketone alkyl substituent is always converted into the carbonyl moiety of the resulting amide regardless of its position relative to the original carbonyl group. Thus, the overall transformation results in the formal reduction of the original carbonyl group to a methylene, and the oxidation of the terminal alkyl carbon to afford an ω-alkylaryl amide (Scheme 55).[‌130‌,‌133‌] The Willgerodt reaction therefore has some formal similarity to the ArndtEistert synthesis (see Section 21.1.5.2).

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