Some compounds along the pathway to unsymmetrically substituted secopentaprismanes

Article abstract of DOI:10.1007/BF01664649

In the preparation of an unsymmetric, polyfunctional [5]-secoprismane hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene were added sequentially to benzoquinone via Diels-Alder reactions. At one point oxidation of the hydroquinone of the diadduct is necessary, and cerium (IV) ammonium nitrate (CAN) is a common oxidizing agent. Oxidation of the diadduct with CAN led to cleavage of the dimethoxy bridge forming a substituted naphthoquinone. The structures of five Diels-Alder adducts and two reaction products of the naphthoquinone are discussed.