Von Braun reaction
Encyclopedia
The Von Braun reaction is an organic reaction
in which a tertiary amine reacts with cyanogen bromide
to an organocyanamide. An example is the reaction of dimethyl-α-naphthylamine
:
The reaction mechanism
consists of two nucleophilic substitution
s: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile.
Organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
in which a tertiary amine reacts with cyanogen bromide
Cyanogen bromide
Cyanogen bromide is a pseudohalogen compound with the formula CNBr. It is a colorless solid that is widely used to modify biopolymers, fragment proteins and peptides, and synthesize other compounds.-Synthesis, basic properties, and structure:...
to an organocyanamide. An example is the reaction of dimethyl-α-naphthylamine
N,N-Dimethyl-1-naphthylamine
N,N-Dimethyl-1-naphthylamine is an aromatic amine. It is formally derived from 1-naphthylamine by replacing the hydrogen atoms on the amino group with methyl groups. N,N-Dimethyl-1-naphthylamine is used in the nitrate reductase test to form a red precipitate of Prontosil by reacting with a...
:
The reaction mechanism
Reaction mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs.Although only the net chemical change is directly observable for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in...
consists of two nucleophilic substitution
Nucleophilic substitution
In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms called the leaving group; the positive or partially positive...
s: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile.