o-Naphthoquinodimethanes and o-Phenanthroquinodimethanes. Isoindene-Related Species

Article abstract of DOI:10.1021/jo00133a013

Three isoindene-related naphthoquinodimethane and phenanthroquinodimethane species were synthesized and trapped with 4-phenyl-1,2,4-triazoline-3,5-dione.They are 2,2-dimethyl-2H-benzindene (3), 2,2-dimethyl-2H-benzindene (4), and 2,2-dimethyl-9H-cyclopentaphenanthrene (10).Compound 3 could be isolated and characterized by ¹H NMR.The effect of solvent on the bisacylation of naphthalene and phenanthrene by dimethylmalonyl chloride is discussed.Also the use of the Vilsmeier reagent generated from PBr3/DMF if highly recommended as a general reagent for conversion of alcohols to alkyl bromides.