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]

Additional recommended knowledge

Don't let static charges disrupt your weighing accuracy

What is the Correct Way to Check Repeatability in Balances?

What is the Sensitivity of my Balance?

This organic reaction was first described by the German chemist Otto Philipp Fischer and Eduard Hepp^[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 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.

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