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Leuckart thiophenol reaction

The Leuckart thiophenol reaction is the decomposition of a diazoxanthate, by gentle warming in a slightly acidic cuprous medium, to its corresponding aryl xanthates which give aryl thiols on alkaline hydrolysis and aryl thioethers on further warming.

This reaction was first reported by Rudolf Leuckart in 1890.

Key Points

The reaction provides a route to introduce Sulfur into aromatic rings.

Products: Aryl Thiols and Aryl Thioethers.

Cu(I) acts as a catalyst to facilitate the decomposition of the diazo intermediate.

Applications

Preparation of Aryl Thiols (Ar–SH): Important in Pharmaceuticals, Dyes, and Agrochemicals.

Synthesis of Aryl Thioethers (Ar–S–Ar): Used in Polymers, Drugs, Materials Chemistry.

Substitution of Diazonium salts with Sulfur groups, expanding the Sandmeyer-resembling transformations.

References