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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Published in:Journal of organic chemistry 2007-04, Vol.72 (8), p.2996-3005
Main Authors: 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
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkenes - chemical synthesis
Alkenes - chemistry
Chemistry
Exact sciences and technology
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Isomerism
Models, Chemical
Models, Molecular
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Thermodynamics
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creator Forman, Mark A
Moran, Caitlin
Herres, Joseph P
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Salandria, Kerry
Gallo, Annemarie
Loutzenhiser, Elizabeth
description 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.
doi_str_mv 10.1021/jo0626313
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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. 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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkenes - chemical synthesis
Alkenes - chemistry
Chemistry
Exact sciences and technology
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Isomerism
Models, Chemical
Models, Molecular
Molecular Structure
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Thermodynamics
title Generation and Reactions of Pentacyclo[4.3.0.02,4.03,8.05,7]non-4-ene
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