For several years, we have been working on the generation, trapping and dimerization of the highly pyramidalized alkene, pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (1). The vicinal diiodide, 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (2), acts as a precursor to 1 via dehalogenation with alkyllithiums. Alkene 1 is very reactive and cannot be isolated, but it can be trapped as its Diels-Alder adduct with various dienophiles. In the absence of a dienophile, the pyramidalized alkene usually dimerizes and undergoes alkyllithium addition reactions. Synthesis of 1 by reductive dehalogenation of 2 with sodium metal yields the cyclobutane dimer and other reduction products.

Synthesis and reactions of pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene

255th National Meeting (2018)

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