Leuckart thiophenol reaction
| Leuckart thiophenol reaction | |
|---|---|
| Named after | Rudolf Leuckart |
| Reaction type | Substitution reaction |
| Identifiers | |
| Organic Chemistry Portal | 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.[1]
This reaction was first reported by Rudolf Leuckart in 1890.[2][3][4]
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
- ^ Kazem-Rostami, Masoud; Khazaei, Ardeshir; Moosavi-Zare, Ahmad; Bayat, Mohammad; Saednia, Shahnaz (2012). "synthesis of thiophenols from related triazenes". Synlett. 23 (13): 1893–1896. doi:10.1055/s-0032-1316557.
- ^ Leuckart, Rudolf (30 December 1889). "Eine neue Methode zur Darstellung aromatischer Mercaptane". Journal für Praktische Chemie. 41 (1): 179–224. doi:10.1002/prac.18900410114.
- ^ Fukushima, D. K.; Tarbell, D. S. (1947). "m-THIOCRESOL". Organic Syntheses. 27: 81. doi:10.15227/orgsyn.027.0081.
- ^ Merck Index 14th Ed.