Hofmann-Löffler reaction

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


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]

Hofmann-Löffler reaction

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

  1. 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.
  2. 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.
  3. March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure (third Edition ed.). John Wiley & Sons. ISBN 0-471-85472-7.
  4. 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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