von Braun reaction
| von Braun reaction | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Named after | Julius von Braun | ||||||||
| Reaction type | Substitution reaction | ||||||||
| Reaction | |||||||||
| |||||||||
The von Braun reaction is an
An example is the reaction ofN,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 second-order nucleophilic substitution (SN2).
See also
References
- .
- .
- ^ J. Org. Chem. 1984, 49, 11, 2081–2082 Publication Date:June 1, 1984 https://doi.org/10.1021/jo00185a072
- ISBN 0-471-60180-2
- ISBN 0471264180.
- S2CID 93616494