Keele Research Repository

The thesis describes the use of polycyclic quinodimethanes
and related compounds as reactive intermediates in the synthesis of polycyclic aromatic and heterocyolic systems, some of which are novel.

Following a general introduction (Chapter I), Chapter II
describes the reactions of 5,6-chrysaquinodimethane to give dimers, and its reactions with various dienophiles; including 1 ,4-naphtho­ quinone, with which it gives a novel ring system. Chapter II describes the reaction of 9,10-phenanthraquinodimethane with 1,4-naphthoquinone and attempts to synthesise 6,12-chrysaquinone from chrysene. The reactions of 9 ,10-anthraquinodimethane with various dienophiles are described (Chapter III) while Chapter IV describes the reactions of 9-methyleneanthrone and 1O-methyl-10-hydroxyanthrone with dimethyl aoetylenedicarboxylate and diethyl azodicarboxylate. Chapter V describes the reactions of 1, 1-diphenylethylene with various dienophiles to give novel adducts; and Chapter VI describes the preparation of endo-adducts of anthranol.