Previously, we have shown that 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane acts as a precursor to the highly pyramidalized alkene pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene via dehalogenation with alkyllithiums. The highly strained and reactive title alkene may be trapped as its Diels-Alder adduct with diphenylisobenzofuran and other conjugated dienes. More recently, we have been investigating new methods for the synthesis of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane as well alternative approaches toward pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene that do not use alkyllithiums, and we will report our progress in these areas.

Pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene: New approaches to a pyramidalized alkene

247th National Meeting (2014)

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