Nasturtium – Tropaeolum

In organic chemistry, the Fischer–Hepp rearrangement is a rearrangement reaction in which an aromatic N-nitroso (−N=O) or secondary nitrosamine (>N−N=O) converts to a carbon nitroso compound:^[1][2]

This organic reaction was first described by the German chemist Otto Philipp Fischer (1852–1932) and Eduard Hepp (June 11, 1851 – June 18, 1917) ^[3] in 1886, and is of importance because para-NO secondary anilines cannot be prepared in a direct reaction.

The rearrangement reaction takes place by reacting the nitrosamine precursor with hydrochloric acid. The chemical yield is generally good under these conditions, but often much poorer if a different acid is used. The exact reaction mechanism is unknown but there is evidence suggesting an intramolecular reaction, similar to that seen in the Bamberger rearrangement.

Sources

• Andraos, John (2000–2012). "Named Things in Chemical Industry" (PDF). Named Things in Chemistry & Physics. Archived (PDF) from the original on 2023-04-07. Retrieved 2024-05-01.

See also

• Friedel–Crafts alkylation-like reactions:
  • Hofmann-Martius rearrangement
  • Fries rearrangement

References