Fischer–Hepp rearrangement

The Fischer–Hepp rearrangement is a rearrangement reaction in which an aromatic N-nitroso or nitrosamine converts to a carbon nitroso compound:[1][2]

Fischer-Hepp rearrangement
Fischer-Hepp rearrangement
Named after Otto Fischer
Eduard Hepp
Reaction type Rearrangement reaction
Identifiers
RSC ontology ID RXNO:0000095

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.

Sources

See also

References
  1. O Fischer, E Hepp. Ber Deutsch chem Ges 19 (1886) p2991
  2. M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)
  3. W Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) ISBN 3817110553
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