Cycloaddition reactions of conjugated dienoic carboxylic acids and esters with N-substituted maleimides and Schiff bases

Khandelwal, G.D.; Wedzicha, B.L.

Cycloaddition reactions of conjugated dienoic carboxylic acids and esters with N-substituted maleimides and Schiff bases

1997

Khandelwal, G.D. | Wedzicha, B.L.

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 C = N bond of Schiff bases could act as a dienophile towards sorbic acid. In general, the 1H chemical shifts for the olefinic protons, originally at C3 and C4 of sorbic acid, are to be found at delta 5.7-5.9 and 6.3-6.5, respectively in the adduct. Those at C2, C5 and C6 are at delta 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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