We have previously shown that pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (2) may be generated via dehalogenation of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (1) with alkyllithiums. The resultant pyramidalized alkene may be trapped as its Diels-Alder adduct with diphenylisobenzofuran (3) and other conjugated 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 approaches toward pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (2), and we will report our progress in this area including the reactions of this highly pyramidalzied alkene.

Reactions of the highly pyramidalized alkene pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.