Previously, we have shown that 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (1) acts as a precursor to the highly pyramidalized alkene pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (2) via dehalogenation with n-butyl and t-butyllithium. We have trapped 2 as its Diels-Alder adduct with diphenylisobenzofuran 3 and other dienes. Recently, we have been investigating new methods for the synthesis of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (1) as well alternative precursors to pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene, and we will report our progress in this area.

Synthesis of precursors to pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (2)

ACS Spring Meeting 2021

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