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
- ^ J. von Braun; K. Heider; E. Müller (1918). "Bromalkylierte aromatische Amine. II. Mitteilung". Chem. Ber. 51 (1): 273–282. doi:10.1002/cber.19180510132.
{{cite journal}}: Unknown parameter|last-author-amp=ignored (|name-list-style=suggested) (help) - ^ Homer W. J. Cressman (1947). "N-Methyl-1-Naphthylcyanamide". Org. Synth. 27: 56. doi:10.15227/orgsyn.027.0056.
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
- ^ Howard A. Hageman (1953). "The Von Braun Cyanogen Bromide Reaction". Organic Reactions. 7 (4): 198–262. doi:10.1002/0471264180.or007.04.