Gomberg-Bachmann reaction
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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.[1][2][3]
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.
[edit] Pschorr reaction
One intramolecular variation which gives better results is the Pschorr reaction [4] [5]:
The group Z can be CH2, CH2CH2, NH and CO (to fluorenone [6]) to name just a few.
[edit] References
- ^ 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)
- ^ R. Pschorr, Chem. Ber. 1896, 29, 496.
- ^ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
- ^ 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
