38658-74-1

Upstream product

• 5210-87-7 1,2,3,4,9,9-hexachloro-1,4-dihydro-1,4-methano-naphthalene-5,8-diol 
• 106-51-4 p-benzoquinone 
• 77-47-4 hexachlorocyclopentadiene 
• 38658-82-1 1,4-dihydro-5,8-acetoxy-1,2,3,4-tetrachloro-1,4-dichloromethanonaphthalene 
• 101312-35-0 1.2.3.4.9.9-hexachloro-(4arH.8acH)-1.4.4a.8a-tetrahydro-1c.4c-methano-naphthalene-quinone-(5.8) 

Relevant academic research and scientific papers

A simple procedure for preparing annulated p-benzoquinones. Improved synthesis of 1,4-dihydro-1,4-methanonaphthalene-5,8-dione

A simple and efficient two-step, one-pot synthesis of substituted 1,4-dihydro-1,4-methanonophthalene-5,8-diones is reported. This synthesis, which utilizes readily available starting materials and inexpensive reagents, can be used to prepare 1a-1c in 70-90% overall yield. This procedure was extended successfully to prepare a more highly complex annulated p-benzoquinone i.e., 8.

Some compounds along the pathway to unsymmetrically substituted secopentaprismanes

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.