Gomberg-Bachmann reaction
- Gomberg-Bachmann reaction
The Gomberg-Bachmann reaction, named for the Ukrainian-American chemist Moses Gomberg and the American chemist Werner Emmanuel Bachmann, is an aryl - aryl coupling reaction via a diazonium salt. [M. Gomberg, W. E. Bachmann. "J. Am. Chem. Soc." 1924, "42", 2339-2343. (DOI|10.1021/ja01675a026)] [W. Pötsch. "Lexikon bedeutender Chemiker" (VEB Bibliographisches Institut Leipzig, 1989) (ISBN 3817110553 )] [M. B. Smith, J. March. "March's Advanced Organic Chemistry" (Wiley, 2001) (ISBN 0-471-58589-0)]
The arene compound 1 (here benzene) is coupled with base with the diazonium salt 2 to the biaryl 3. Many aromats have been tested but yields are generally low (less than 40%) given the many side-reactions of diazonium salts.
Pschorr reaction
One intramolecular variation which gives better results is the Pschorr reaction [R. Pschorr, Chem. Ber. 1896, 29, 496.] [JerryMarch] :
The group Z can be CH2, CH2CH2, NH and CO (to fluorenone ["Sandmeyer reactions. Part 5.1 Estimation of the rates of 1,5-aryl/aryl radical translocation and cyclisation during Pschorr fluorenone synthesis with a comparative analysis of reaction energetics" Stephen A. Chandler,a Peter Hanson, Alec B. Taylor, Paul H. Walton and Allan W. Timmsb J. Chem. Soc., Perkin Trans. 2, 2001, 214–228 DOI|10.1039/b006184k ] ) to name just a few.
References
ee also
* Graebe-Ullmann synthesis
* Meerwein arylation
* Sandmeyer reaction
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