Author(s) |
Digianantonio, Katherine M
Glover, Stephen
Johns, Jennifer
Rosser, Adam Andrew
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Publication Date |
2011
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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.
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Citation |
Organic & Biomolecular Chemistry, 9(11), p. 4116-4126
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ISSN |
1477-0539
1477-0520
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Link | |
Publisher |
Royal Society of Chemistry
|
Title |
Synthesis and thermal decomposition of N,N-dialkoxyamides
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Type of document |
Journal Article
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Entity Type |
Publication
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