38658-82-1Relevant academic research and scientific papers
Some compounds along the pathway to unsymmetrically substituted secopentaprismanes
Sun, Duoli,Watson, William H.
, p. 721 - 737 (1996)
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.
