1,5-Anhydro-4-deoxy- d- glycero-hex-1-en-3-ulose and other pyrolysis products of cellulose

Abstract

Uncatalyzed pyrolysis of cellulose provides a tar containing mainly 1,6-anhydro- d-glucose derivatives and some unsaturated products. The latter include a new enone that has been isolated by preparative column chromatography in 1.4% yield and identified as 1,5-anhydro-4-deoxy- d- glycero-hex-l-en-3-ulose. This compound is also formed by pyrolysis of other carbohydrate polymers. A mechanism for its production from internal units has been deduced from the experimental data. The pyrolysis products of cellulose also contain 3,5-dihydroxy-2-methyl-4 H-pyran-4-one, which appears to be an oxidation product.