Chemical Sciences: A Manual for CSIR-UGC National Eligibility Test for Lectureship and JRF/Named Reactions/Hofmann-Loffor-Freytage 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]

An example is the synthesis of n-butylpyrrolidine:[3]

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[edit]

  1. doi:10.1002/cber.188301601120
  2. doi:10.1002/cber.19090420377
  3. Organic Syntheses, Coll. Vol. 3, p.159 (1955); Vol. 25, p.14 (1945). http://www.orgsynth.org/orgsyn/pdfs/CV3P0159.pdf