Hunsdiecker reaction

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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 Hunsdiecker reaction

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

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

[edit] Reaction mechanism

The reaction mechanism of the Hunsdiecker reaction is believed to involved 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.

The mechanism of the Hunsdiecker reaction

[edit] 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. ↑  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)

[edit] See also

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