Allylic iodides react with silver trichloroacetate in the presence of furans of form allyfurans in up to 40% yield in a general reaction. In contrast prop-2-ynyl iodide gave methyl 5-prop-2-ynyl-3-furoate (9) from methyl 3-furoate (1) in ca. 1% yield. A hydroxymethyl group attached to C-3 favours substitution at C-2 rather than C-5, whereas a methoxycarbonyl group exerts the reverse orientational effect.
H. M. R. Hoffmann and N. F. Janes, J. Chem. Soc. C, 1969, 1456 DOI: 10.1039/J39690001456
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