von Braun reaction
Template:Reactionbox 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 N,N-dimethyl-1-naphthylamine:[2]
These days, most chemist have replaced cyanogen bromide reagent with chloroethyl chloroformate reagent instead. It appears as though Olofson et al. was the first chemist to have reported this.[3]
Reaction mechanism
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.[4][5] In following the mechanism is described using trimethylamine as example:[6]
First, the trimethylamine reacts with the cyanogen bromide to form a quaternary ammonium salt, which in the next step reacts by splitting off bromomethane to give the dimethylcyanamide. This is a bimolecular nucleophilic substitution (SN2).
See also
References
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- ↑ J. Org. Chem. 1984, 49, 11, 2081–2082 Publication Date:June 1, 1984 https://doi.org/10.1021/jo00185a072
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