Structure Elucidation of Alkaloids

Von Braun Degradation Method

• The von Braun reaction is a reaction in which a tertiary
amine reacts with cyanogen bromide to an organocyana
amide. For example

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. For
example
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 Structure Elucidation of Alkaloids
Von Braun Degradation Method

• First, the amine reacts with the cyanogen bromide to form a

cyano group. This results in 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)

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 Structure Elucidation of Alkaloids
Von Braun Degradation Method
• The von Braun amide degradation is the chemical reaction of a
mono substituted amide with phosphorous pentachloride or
thionyl chloride to give a nitrile and an organo halide. It is
named after Julius Jacob von Braun, who first reported the
reaction.

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