Wohl–Ziegler bromination: Difference between revisions
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Best yields are achieved with [[N-Bromosuccinimide|''N''-bromosuccinimide]] in [[carbon tetrachloride]] solvent. |
Best yields are achieved with [[N-Bromosuccinimide|''N''-bromosuccinimide]] in [[carbon tetrachloride]] solvent. |
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Several reviews have been published.<ref>{{cite journal | author = [[Carl Djerassi|C. Djerassi]] | title = Brominations with N-Bromosuccinimide and Related Compounds. The Wohl-Ziegler Reaction | year = 1948 | journal = [[Chem. Rev.]] | volume = 43 | issue = 2 | pages = 271–317 | doi = 10.1021/cr60135a004}}</ref><ref>Horner, L.; Winkelman, E. M. |
Several reviews have been published.<ref>{{cite journal | author = [[Carl Djerassi|C. Djerassi]] | title = Brominations with N-Bromosuccinimide and Related Compounds. The Wohl-Ziegler Reaction | year = 1948 | journal = [[Chem. Rev.]] | volume = 43 | issue = 2 | pages = 271–317 | doi = 10.1021/cr60135a004}}</ref><ref>{{cite journal | author = Horner, L.; Winkelman, E. M. | journal = [[Angew. Chem.]] | year = 1959 | volume = 71 | pages = 349}}</ref> |
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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 CCl<sub>4</sub>, 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. |
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 CCl<sub>4</sub>, 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. |
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Revision as of 13:32, 30 September 2009
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
{{cite journal}}: CS1 maint: multiple names: authors list (link); 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.
- ^ Horner, L.; Winkelman, E. M. (1959). Angew. Chem. 71: 349.
{{cite journal}}: Missing or empty|title=(help)CS1 maint: multiple names: authors list (link)