Wohl–Ziegler bromination: Difference between revisions
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is a [[chemical reaction]] that involves the [[allylic]] or [[benzylic]] [[bromination]] of [[hydrocarbon]]s using an ''N''-bromoimide and a [[radical initiator]].<ref>{{OrgSynth | |
is a [[chemical reaction]] that involves the [[allylic]] or [[benzylic]] [[bromination]] of [[hydrocarbon]]s using an ''N''-bromoimide and a [[radical initiator]].<ref>{{OrgSynth |author1=Greenwood, F. L.|author2=Kellert, M. D.|author3=Sedlak, J. |year=1963 |title=4-Bromo-2-heptene |collvol=4 |collvolpages=108 |prep=cv4p0108}}</ref> |
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:[[Image:NBS Allylic Bromination Scheme.png|400px|The Wohl-Ziegler reaction]] |
:[[Image:NBS Allylic Bromination Scheme.png|400px|The Wohl-Ziegler reaction]] |
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Revision as of 21:59, 26 December 2016
| Wohl-Ziegler bromination | |
|---|---|
| Named after | Alfred Wohl Karl Ziegler |
| Reaction type | Substitution reaction |
| Identifiers | |
| Organic Chemistry Portal | wohl-ziegler-reaction |
| RSC ontology ID | RXNO:0000225 |
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 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
- ^ Alfred Wohl (1919). "Bromierung ungesättigter Verbindungen mit N-Brom-acetamid, ein Beitrag zur Lehre vom Verlauf chemischer Vorgänge". Berichte der deutschen chemischen Gesellschaft. 52: 51–63. doi:10.1002/cber.19190520109.
- ^ Ziegler, K., G. Schenck, E. W. Krockow, A. Siebert, A. Wenz, H. Weber (1942). "Die Synthese des Cantharidins". Justus Liebig's Annalen der Chemie. 551: 1–79. doi:10.1002/jlac.19425510102.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Greenwood, F. L.; Kellert, M. D.; Sedlak, J. (1963). "4-Bromo-2-heptene". Organic Syntheses; Collected Volumes, vol. 4, p. 108.
- ^ C. Djerassi (1948). "Brominations with N-Bromosuccinimide and Related Compounds. The Wohl–Ziegler Reaction". Chem. Rev. 43 (2): 271–317. doi:10.1021/cr60135a004. PMID 18887958.
- ^ Horner, L; Winkelman, E. M (1959). "Neuere Methoden der präparativen organischen Chemie II 14. N-Bromsuccinimid, Eigenschaften und Reaktionsweisen Studien zum Ablauf der Substitution XV". Angew. Chem. 71: 349. doi:10.1002/ange.19590711102.