Azonia polycyclic quinones,o-diazo-oxides and related products

4α-Azoniaanthracene-5,6- and 5,8-dione salts have been prepared by nitric acid oxidation of their respective diols, and are shown to function as either an electrophilic dienophile or a diene component in Diels-Alder-type reactions. Several azonia o-quinones have been treated with tosylhydrazine in methanol saturated with hydrogen chloride to give unusually stable o-diazo-oxides. A four-step dehydroxylation procedure is detailed for the conversion of .5,6-dihydroxy-4α-azonia-anthracene salts to new 5-hydroxy-4α-azoniaanthracene salts.