Chemistry of anti- and syn-1,2:3,4-Naphthalene Dioxides and Their Potential Relevance as Metabolic Intermediates

Article abstract of DOI:10.1021/jo00148a021

The reactivity, site of attack, and stereochemistry of reactions of a variety of nucleophiles with the anti- and syn-1,2:3,4-naphthalene dioxides have been explored.In most cases, substituted tetrahydronaphthalene products arising through attack at the C-1 and C-4 positions in the anti mode were obtained.These isomeric dioxides provide excellent precursors for a number of difficultly accessible 1,4-disubstituted naphthalene derivatives such as 1,4-diphenoxynaphthalene and 1,4-dicyanonaphthalene.Evidence is also presented that anti-naphthalene dioxide constitutes an intermediate metabolite in the rat.