Please use this identifier to cite or link to this item:
https://hdl.handle.net/1959.11/199
Title: | The HERON Reaction: Origin, theoretical background, and prevalence | Contributor(s): | Glover, S (author) ; Rauk, A (author); Buccigross, JM (author); Campbell, JJ (author); Hammond, GP (author); Mo, G (author); Andrews, L (author); Gillson, A (author) | Publication Date: | 2005 | Open Access: | Yes | DOI: | 10.1139/V05-150 | Handle Link: | https://hdl.handle.net/1959.11/199 | 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. | Publication Type: | Journal Article | Source of Publication: | Canadian Journal of Chemistry, 83(9), p. 1492-1509 | Publisher: | Canadian Science Publishing | Place of Publication: | Canada | ISSN: | 1480-3291 0008-4042 |
Fields of Research (FoR) 2008: | 030505 Physical Organic Chemistry | Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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Appears in Collections: | Journal Article |
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open/SOURCE01.pdf | Publisher version (open access) | 495.72 kB | Adobe PDF Download Adobe | View/Open |
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