Fischer–Hepp rearrangement

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

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

This organic reaction was first described by the German chemist Otto Philipp Fischer (1852–1932 ) and Eduard Hepp (June 11, 1851 – June 18, 1917) 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.

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