Degradation of carbohydrates. V. Isolation of intermediates in the formation of 5-(Hydroxymethyl)-2-furaldehyde

Abstract

3-Deoxyhexosuloses and 3,4-dideoxyhexosulos-3-enes have been isolated as intermediates in the formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose and L-sorbose. Some new derivatives of these compounds have been prepared including isopropylidene derivatives of their 2,4-dinitrophenylosazones. The isolations support a mechanism previously reported and permit an assessment of the relative importance of the different pathways.