Convenient Synthesis of Some Functionalized Dewar Benzenes and Effect of Chlorine Substitution on the Rates of Their Aromatization

Article abstract of DOI:10.1246/cl.1990.1193

1,4-Bis(hydroxymethyl) Dewar benzenes were prepared in five steps from dimethyl acetylenedicarboxylate in ca. 10percent overall yield and rates of their aromatization were measured: dichloro substitution at both the 2,5- and 2,6-positions led to substantial deceleration of the isomerization.