Hofmann-Löffler reaction
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The Hofmann-Löffler reaction or Hofmann-Löffler-Freytag Reaction is an organic reaction is which a haloamine is converted to a cyclic amine such as a pyrrolidine with heat and an acid [1][2][3]
An example is the synthesis of n-butylpyrrolidine [4]
The reaction type is a radical substitution. In the first step the halogen atom migrates from nitrogen to a gamma or delta carbon position in a rearrangement reaction.
A conceptually related reaction is the Barton reaction.
References
- ↑ August Wilhelm von Hofmann (1883). "Ueber die Einwirkung des Broms in alkalischer Lösung auf die Amine (p )". Berichte der deutschen chemischen Gesellschaft 16 (1): 558–560. doi:10.1002/cber.188301601120.
- ↑ Karl Löffler, Curt Freytag (1909). "Über eine neue Bildungsweise von N-alkylierten Pyrrolidinen". Berichte der deutschen chemischen Gesellschaft 42 (3): 3427–3431. doi:10.1002/cber.19090420377.
- ↑ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7.
- ↑ Organic Syntheses, Coll. Vol. 3, p.159 (1955); Vol. 25, p.14 (1945). http://www.orgsynth.org/orgsyn/pdfs/CV3P0159.pdf
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