Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/8299
Title: Synthesis and thermal decomposition of N,N-dialkoxyamides
Contributor(s): Digianantonio, Katherine M (author); Glover, Stephen  (author)orcid ; Johns, Jennifer (author); Rosser, Adam Andrew  (author)orcid 
Publication Date: 2011
DOI: 10.1039/c1ob00008j
Handle Link: https://hdl.handle.net/1959.11/8299
Abstract: N,N-Dialkoxyamides 1c, a virtually unstudied member of the new class of anomeric amides, amides bearing two electronegative atoms at nitrogen, have been synthesised in useful yields directly from hydroxamic esters using phenyliodine(III)bis(trifluoroacetate) (PIFA). Infrared carbonyl stretch frequencies and carbonyl ¹³C NMR properties have been reported, which support strong inhibition of amide resonance in these amides. Their thermal decomposition reactions in mesitylene at 155°C proceed by homolysis to form alkoxyamidyl and alkoxyl free radicals in preference to HERON rearrangements to esters. The reactions follow first-order kinetics and for a series of N,N-dimethoxy-4-substituted benzamides, activation energies of 125–135 kJ mol⁻¹ have been determined together with weakly negative entropies of activation.
Publication Type: Journal Article
Source of Publication: Organic & Biomolecular Chemistry, 9(11), p. 4116-4126
Publisher: Royal Society of Chemistry
Place of Publication: United Kingdom
ISSN: 1477-0539
1477-0520
Fields of Research (FoR) 2008: 030501 Free Radical Chemistry
030505 Physical Organic Chemistry
Socio-Economic Objective (SEO) 2008: 970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article

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