3-Oxidopyrylium adducts from the pyrolysis of cellulose

Abstract

The major product from pyrolysis of acid-doped cellulose is levoglucosenone (1) which is now shown to undergo, under the conditions of its formation, deformylation to 3-oxidopyrylium (2). Five dimers [(7), (9), (11), (14) and either (10) or (16)] of this ylide (2), and an adduct (17) of it and levoglucosenone (1), have now been isolated from the product of phosphoric acid-catalysed pyrolysis of cellulose. Sealed tube pyrolysis of (1) yielded the adduct (17) and its isomer (18).