Issue 0, 1968

Diels–Alder reactions of long-chain unsaturated fatty acids

Abstract

Methyl 9,12-dioxo-octadeca-trans-10-enoate undergoes Diels-Alder reaction with isoprene, with 2,3-dimethylbutadiene, and with methyl octadeca-trans-9,trans-11-dienoate to give substituted cyclohexenes. Clemmensen reduction of the cycloaddition product from the last-mentioned compound does not proceed normally, but yields a dihydroisobenzofuran compound by cyclodehydration. Diels–Alder reaction of 12-oxo-octadec-trans-10-enoic acid and octadeca-trans-9,trans-11-dienoic acid does not proceed to completion, but Clemmensen reduction of the cycloaddition product occurs normally to give the C36 cyclic di-acid.

Article information

Article type
Paper

J. Chem. Soc. C, 1968, 1781-1784

Diels–Alder reactions of long-chain unsaturated fatty acids

G. F. Whitfield, J. Chem. Soc. C, 1968, 1781 DOI: 10.1039/J39680001781

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