von Braun reaction

The von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide.[1] An example is the reaction of dimethyl-α-naphthylamine:[2]

The reaction mechanism consists of two nucleophilic substitutions: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile.[3][4]


See also

References

  1. ↑ J. von Braun, K. Heider, and E. Müller (1918). "Bromalkylierte aromatische Amine. II. Mitteilung". Chem. Ber. 51 (1): 273–282. doi:10.1002/cber.19180510132.
  2. ↑ Homer W. J. Cressman (1947). "N-Methyl-1-Naphthylcyanamide". Org. Synth. 27: 56. doi:10.15227/orgsyn.027.0056.
  3. ↑ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7
  4. ↑ Howard A. Hageman (1953). "The Von Braun Cyanogen Bromide Reaction". Organic Reactions 7 (4): 198–262. doi:10.1002/0471264180.or007.04.
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