Abstract
Sorbic acid and its esters were investigated as potential dienes in Diels-Alder reactions with N-substituted maleimides. The purpose was to characterise such Diels-Alder adducts by means of NMR, and to provide reference compounds to identify the formation of related products in model food systems. These reactions occur both in aqueous and non-aqueous systems and it is possible that the CN bond of Schiff bases could act as a dienophile towards sorbic acid. In general, the 1 H chemical shifts for the olefinic protons, originally at C 3 and C 4 of sorbic acid, are to be found at δ 5.7–5.9 and 6.3–6.5, respectively in the adduct. Those at C 2, C 5 and C 6 are at δ 2.4–2.6, 3.4–4.2 and 1.4–1.5, respectively. All these values are characteristically different from the corresponding proton chemical shifts in sorbic acid.
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