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Reaction of Bromine with Silver (+)-α-Phenylpropionate : an Electrophilic Bimolecular Substitution

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Abstract

IN a review of the literature of the reactions of the silver salts of carboxylic acids with bromine, Kleinberg1 has concluded that when one equivalent of salt reacts with two of bromine, an intermediate compound R.COOBr is formed, which decarboxylates to give the bromide RBr, and from the addition of R.COOBr to olefins and other reactions, that the bromine atom reacts as a 'positive' halogen.

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References

  1. Kleinberg, J., Chem. Rev., 40, 381 (1947).

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  2. Gerrard, W., J. Chem. Soc., 741 (1946).

  3. Arcus, C. L., and Kenyon, J., J. Chem. Soc., 916 (1939). Kenyon, J., and Young, D. P., ibid., 263 (1941). Campbell, A., and Kenyon, J., ibid., 25 (1946).

  4. Holmberg, B., Ber., 45, 997 (1912). Campbell, A. (unpublished results).

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  5. Hughes, E. D., Ingold, C. K., and Scott, A. D., J. Chem. Soc., 1201 (1937).

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ARCUS, C., CAMPBELL, A. & KENYON, J. Reaction of Bromine with Silver (+)-α-Phenylpropionate : an Electrophilic Bimolecular Substitution. Nature 163, 287–288 (1949). https://doi.org/10.1038/163287b0

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