Written by J.A Dobado | Last Updated on September 15, 2025
What is HERON rearrangement?
The HERON rearrangement, which stands for HEteroatom Rearrangements On Nitrogen, is a chemical reaction that involves the migration of oxygen from the nitrogen atom to the carbonyl carbon in bisheteroatom-substituted amides. This reaction leads to the formation of esters and 1,1-diazenes. Additionally, analogues of N,N’-diacyl-N,N’-dialkoxyhydrazines undergo thermal decomposition, which involves two consecutive rearrangements, ultimately producing esters and N2.
References
- Buccigross JM , Glover SA Rowbottom CA (1995) Decomposition of N,N’-Diacyl-N,N’-dialkoxyhydrazines Revisited. Australian Journal of Chemistry 48, 353-361.
DOI: 10.1071/CH9950353 - J. M. Buccigross, S. A. Glover, “Molecular orbital studies of novel N to C migrations in N,N-bisheteroatom-substituted amides—HERON rearrangements” J. Chem. Soc., Perkin Trans. 2, 1995, 595-603
DOI: 10.1039/P29950000595
Full Professor of Organic Chemistry at the University of Granada, with a long-standing research career in Computational Chemistry and molecular modeling and design.