Hunsdiecker reaction
From Wikipedia, the free encyclopedia
The Hunsdiecker reaction (also called the Borodin reaction after Alexander Borodin) is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides.[1][2][3][4] The reaction is named after Heinz Hunsdiecker and Cläre Hunsdiecker.
Several reviews have been published.[5][6]
Mercuric oxide will also effect this transformation.[7][8]
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[edit] Reaction mechanism
The reaction mechanism of the Hunsdiecker reaction is believed to involve organic radical intermediates. The silver salt of the carboxylic acid 1 will quickly react with bromine to form intermediate 2. Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4, which will quickly recombine to form the desired organic halide 5.
[edit] Variations
[edit] Simonini reaction
The reaction of silver salts of carboxylic acids with iodine is called the Simonini reaction , named after Angelo Simonini a student of Adolf Lieben at the University of Vienna.[9][10][5]
[edit] References
- ^ Cläre Hunsdiecker, et al. U.S. Patent # 2,176,181.
- ^ Heinz Hunsdiecker; Cläre Hunsdiecker Ber. 1942, 75, 291.doi:10.1002/cber.19420750309
- ^ Borodin, A. Ann. 1861, 119, 121.doi:10.1002/jlac.18611190113 10.1002/jlac.18611190113
- ^ Allen, C. F. H.; Wilson, C. V. Organic Syntheses, Coll. Vol. 3, p.578 (1955); Vol. 26, p.52 (1946). (Article)
- ^ a b Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219. (Review)
- ^ Wilson, C. V. Org. React. 1957, 9, 341. (Review)
- ^ Meek, J. S.; Osuga, D. T. Organic Syntheses, Coll. Vol. 5, p.126 (1973); Vol. 43, p.9 (1963). (Article)
- ^ Lampman, G. M.; Aumiller, J. C. Organic Syntheses, Coll. Vol. 6, p.179 (1988); Vol. 51, p.106 (1971). (Article)
- ^ Simonini, A. (1892). "Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen". Monatshefte für Chemie 13 (1): 320–325. doi:.
- ^ Simonini, A. (1893). "Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen". Monatshefte für Chemie 14 (1): 80–92. doi:.
