Fischer-Hepp rearrangement

Encyclopedia : F : FI : FIS : 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 Phillipp Fischer and Eduard Hepp W Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) (ISBN 3-323-00185) 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 but with other acids results are poor. The exact reaction mechanism is unknown but there is evidence suggesting a intramolecular reaction.

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