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Wohl-Ziegler reaction
Introduction
The Wohl-Ziegler reaction[1][2] is a chemical reaction that involves the allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator.[3]
Best yields are achieved with N-bromosuccinimide in carbon tetrachloride solvent.
Several reviews have been published.[4][5]
In a typical setup a a stoichiometric amount of N-bromosuccinimide solution and a small quantity of initiator are added to a solution of the substrate in CCl4, and the reaction mixture is stirred and heated to the boiling point. Initiation of the reaction is indicated by more vigorous boiling; sometimes the heat source may need to be removed. Once all N-bromosuccinimide (which is denser than the solvent) has been converted to succinimide (which floats on top) the reaction has finished.
References
- ↑ Wohl, A. Ber. 1919, 52, 51.
- ↑ Ziegler, K.; et al. Ann. 1942, 551, 30.
- ↑ Template:OrgSynth
- ↑ C. Djerassi (1948). “Brominations with N-Bromosuccinimide and Related Compounds. The Wohl-Ziegler Reaction”. Chem. Rev. 43 (2): 271–317. doi:10.1021/cr60135a004.
- ↑ Horner, L.; Winkelman, E. M.; Angew. Chem. 1959, 71, 349. (Review)