Effect of carbonyl and alkoxycarbonyl groups on the direction of the hydrogenolysis of the furan ring under the conditions of vapor-phase hydrogenation

Abstract

1. An investigation was made of the effect of side-chain carbonyl and alkoxycarbonyl groups in the γ-position with respect to the furan nucleus and separated from it by -C-C- or -C=C- on the position at which the furan ring opens in the vapor-phase hydrogenation of the compound over a platinum catalyst. 2. 4-(2-Furyl)-2-butanone and ethyl 2-furanpropionate undergo hydrogenolysis with opening of the furanring mainly at the C-O bond remote from the side chain (92–93%). In contrast to this, the furan ring in 4-(2-furyl)-3-buten-2-one and ethyl 2-furanacrylate is opened in this way to the extent of 60–65%, but is opened at the C- O bond adjacent to the side chain to the extent of 30–40%.