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Hunsdiecker reaction



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]

Several reviews have been published.[5][6]

Mercuric oxide will also affect this transformation.[7][8]

Additional recommended knowledge

Contents

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.

Variations

Simonini reaction

The reaction of silver salts of carboxylic acids with iodine is called the Simonini reaction.[9][10][5]

References

  1. ^ Hunsdiecker, C. et al. U.S. Patent # 2,176,181.
  2. ^ Hunsdiecker, H.; Hunsdiecker, C. Ber. 1942, 75, 291.
  3. ^ Borodin, A. Ann. 1861, 119, 121.
  4. ^ Allen, C. F. H.; Wilson, C. V. Organic Syntheses, Coll. Vol. 3, p.578 (1955); Vol. 26, p.52 (1946). (Article)
  5. ^ a b Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219. (Review)
  6. ^ Wilson, C. V. Org. React. 1957, 9, 341. (Review)
  7. ^ Meek, J. S.; Osuga, D. T. Organic Syntheses, Coll. Vol. 5, p.126 (1973); Vol. 43, p.9 (1963). (Article)
  8. ^ Lampman, G. M.; Aumiller, J. C. Organic Syntheses, Coll. Vol. 6, p.179 (1988); Vol. 51, p.106 (1971). (Article)
  9. ^ Simonini, A. Monatsh. 1892, 13, 320.
  10. ^ Simonini, A. Monatsh. 1893, 14, 81.

See also

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Hunsdiecker_reaction". A list of authors is available in Wikipedia.
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