Wohl-Ziegler reaction
From Wikipedia, the free encyclopedia
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.
[edit] References
- ^ Wohl, A. Ber. 1919, 52, 51.
- ^ Ziegler, K.; et al. Ann. 1942, 551, 30.
- ^ Greenwood, F. L.; Kellert, M. D.; Sedlak, J. Organic Syntheses, Coll. Vol. 4, p.108 (1963); Vol. 38, p.8 (1958). (Article)
- ^ Djerassi, C.; Chem. Rev. 1948, 43, 271. (Review) DOI
- ^ Horner, L.; Winkelman, E. M.; Angew. Chem. 1959, 71, 349. (Review)
