Synthesis and Chemistry of Some Tricyclic Cyclopropenes. 3. Tricyclo2,4>oct-2(4)-ene

Article abstract of DOI:10.1021/jo00048a032

The title compound cyclopropene 2 has been synthesized in situ from dibromide 8 and diiodide 9 via dehalogenation of tert-butyllithium in THF at -78 deg C.The dihalides were formed in six steps starting with cyclopentadiene and (chloromethyl)maleic anhydride.In the presence of diphenylisobenzofuran (DPIBF) 2 forms a Diels-Alder adduct, most probably 10.Cyclopropene 2 and a previously synthesized cyclopropene 1 were decomposed under these same conditions, only without DPIBF present, to give complex mixtures of products, some of which were characterized as tert-butyl adducts and dimers via the ene reaction of the cyclopropenes.