Tautomeric benz[de]anthracene derivatives and related systems

Abstract

Intramolecular Friedel–Crafts acylation of β-9-anthrylpropionic acid gives 1,2-dihydrobenz[de]anthracen-3-one (II) in agreement with earlier work. This product is readily converted into derivatives of the tautomeric 3-hydroxy-7H-benz[de]anthracene (VI; R = OH) and oxidised to the somewhat unstable benz[de]anthracen-3-one (IV). 1,2,7,8-Tetrahydroperylene-3,9-dione (IX), obtained by cyclisation of ββ′-9,10-anthryldipropionic acid, is also readily oxidised; on acetylation it forms 3,9-diacetoxyperylene, a product previously formulated as a dienol acetate. Spectroscopic comparison of the cyclic ketones (IX) and (II) with their acyclic analogues, 1,5-diacetyl- and 1-acetyl-anthracene respectively, indicates considerable difference between the two series in the preferred orientation of carbonyl groups with respect to the anthracene system.