Fischer-Hepp rearrangement
- 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: [ O Fischer, E Hepp. "Ber Deutsch chem Ges" 19 (1886) p2991] [ M B Smith, J March. "March's Advanced Organic Chemistry" (Wiley, 2001) (ISBN 0-471-58589-0)]
This organic reaction was first described by the German chemist Otto Philipp Fischer and Eduard Hepp (June 11, 1851-June 18, 1917) [ W Pötsch. "Lexikon bedeutender Chemiker" (VEB Bibliographisches Institut Leipzig, 1989) (ISBN 3817110553 ] 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 in general are 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.
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