First preparation of an acetal of buta-2,3-dienal, the simplest, so far unknown, allenic aldehyde

Abstract

A crystalline, six-membered, cyclic acetal of buta-2,3-dienal was obtained in 83% yield by the treatment of 3-O-(Z-but-1-en-3-ynyl)-1,2-O-isopropylidene-α-D-glucofuranose with potassium hydroxide, and in 31% yield by the mild, acidic hydrolysis of 3-O-(E-but-1-en-3-ynyl)-1,2; 5,6-di-O-isopropylidene-α-D-glucofuranose.