A Neutral Donor-Acceptor p-Stack: Solid-State Structures of 1 : 1 Pyromellitic Diimide-Dialkoxynaphthalene Cocrystals

Abstract

Substituted ortho-benzoquinones, generated in situ by hypervalent iodine oxidation of catechols, are intercepted by unsymmetrical dienes to provide Diels-Alder adducts with complete regiospecificity. Catechols with carboxy substituents in the 3 or 4 positions react similarly and the initial adducts decarboxylate to produce 8-substituted or 5-substituted 1,2-dihydroxydihydronaphthalenes respectively, in a one-pot three-step sequence. The reaction has been further adapted to produce naphtho[1,8-bc]furans in a one-pot process; its application towards the synthesis of the tricyclic system of the sesquiterpene nardonoxide is described