We have previously reported that 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane(1) acts as a precursor to the pyramidalized alkene pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (2) via dehalogenation with alkyllithiums, as 2 may be trapped as its Diels-Alder adduct 3 with diphenylisobenzofuran. Reductive dehalogenation of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (1) with sodium metal yields several products, including the cyclobutane dimer. 

Reductive dehalogenation of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane: Cyclobutane dimers

241st National Meeting (2011)

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