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Generation and reactions of Pentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene.

The Journal of organic chemistry (2007-03-16)
Mark A Forman, Caitlin Moran, Joseph P Herres, Jason Stairs, Emily Chopko, Anthony Pozzessere, Michael Kerrigan, Carisa Kelly, Lisa Lowchyj, Kerry Salandria, Annemarie Gallo, Elizabeth Loutzenhiser
ABSTRACT

The highly pyramidalized alkene, pentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]non-4-ene (9), has been generated via treatment of 4,5-diiodopentacyclo[4.3.0.0(2,4).0(3,8).0(5,7)]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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
n-Butyllithium solution, 2.7 M in heptane
Sigma-Aldrich
n-Butyllithium solution, 2.5 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 2.0 M in cyclohexane
Sigma-Aldrich
n-Butyllithium solution, 1.6 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 11.0 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 1.4 M in toluene