Generation and Reactions of Pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene

The highly pyramidalized alkene, pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (9), has been generated via treatment of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (12) with n-butyllithium and tert-butyllithium. The title alkene has also been trapped as its Diels−Alder adduct with 1,3-diphenylisobe...

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Veröffentlicht in:Journal of organic chemistry 2007-04, Vol.72 (8), p.2996-3005
Hauptverfasser: Forman, Mark A, Moran, Caitlin, Herres, Joseph P, Stairs, Jason, Chopko, Emily, Pozzessere, Anthony, Kerrigan, Michael, Kelly, Carisa, Lowchyj, Lisa, Salandria, Kerry, Gallo, Annemarie, Loutzenhiser, Elizabeth
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Sprache:eng
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Zusammenfassung:The highly pyramidalized alkene, pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene (9), has been generated via treatment of 4,5-diiodopentacyclo[4.3.0.02,4.03,8.05,7]nonane (12) with n-butyllithium and tert-butyllithium. The title alkene has also been trapped as its Diels−Alder adduct with 1,3-diphenylisobenzofuran, 2,5-dimethylfuran, and spiro[2.4]hepta-4,6-diene. Products resulting from alkyllithium addition to the pyramidalized double bond of 9 have been isolated and fully characterized spectroscopically. The geometry, olefin strain energy, heat of hydrogenation, and relative HOMO/LUMO energies of 9 have been obtained by ab initio calculations at the MP2 and B3LYP levels using the 6-31G* basis set.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0626313