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157:: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile. In following the mechanism is described using
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First, the trimethylamine reacts with the cyanogen bromide to form a quaternary ammonium salt, which in the next step reacts by splitting off
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reagent instead. It appears as though
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Name reactions: A collection of detailed mechanisms and synthetic applications
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Howard A. Hageman (1953). "The Von Braun
Cyanogen Bromide Reaction".
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These days, most chemist have replaced cyanogen bromide reagent with
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J. Org. Chem. 1984, 49, 11, 2081–2082 Publication Date:June 1, 1984
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Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
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Homer W. J. Cressman (1947). "N-Methyl-1-Naphthylcyanamide".
358:(in German) (5th ed.), Cham: Springer, p. 619,
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to give the dimethylcyanamide. This is a second-order
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218:"Bromalkylierte aromatische Amine. II. Mitteilung"
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295:(4th ed.), New York: Wiley, p. 436–7,
216:J. von Braun; K. Heider & E. Müller (1918).
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155:nucleophilic substitutions
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177:nucleophilic substitution
139:chloroethyl chloroformate
125:-dimethyl-1-naphthylamine
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36:Substitution reaction
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19:von Braun reaction
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151:reaction mechanism
145:Reaction mechanism
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318:Organic Reactions
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24:Named after
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223:Chem. Ber.
203:References
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291:(1992),
191:See also
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257:: 56.
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185:2
183:N
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123:N
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119:N
71:↓
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