| Title |
|
The HERON Reaction: Origin, theoretical background, and prevalence |
|
|
| Publication Date |
|
| Author(s) |
|
| Type of document |
|
| Language |
|
| Entity Type |
|
| Publisher |
|
Canadian Science Publishing |
|
|
| Place of publication |
|
| DOI |
|
| UNE publication id |
|
| Abstract |
|
The origin of the HERON reaction is reviewed from a historical perspective and shown to have its foundation in the unusual properties of bisheteroatom-substituted amides, so-called anomeric amides. The reaction involves migration of anomerically destabilized oxo-substituents on an amide nitrogen to the amide carbon and dissociation of the amide bond. Computational work providing a theoretical basis for the reaction is presented, together with physical organic measurements that support results therefrom. The rearrangement has been observed in a number of chemicaltransformations of N-alkoxy-N-aminoamides, reactions of 1-acyloxy-1-alkoxydiazenes, N-alkoxy-N-aminocarbamates, Nalkoxyhydroxamicacids, as well as in the gas-phase reactions of N-acyloxy-N-alkoxyamides. |
|
|
| Link |
|
| Citation |
|
Canadian Journal of Chemistry, 83(9), p. 1492-1509 |
|
|
| ISSN |
|
| Start page |
|
| End page |
|