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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
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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: National Research Council, Canada
Place of Publication: Ottawa, Canada
ISSN: 0008-4042
Field of Research (FOR): 030505 Physical Organic Chemistry
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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