ORGN 382 |
Benzo-13-arylphenalene: A progress report
| Jelena Zivkovic and Klaus G. Grohmann. Chemistry Department, Hunter College & Graduate Center of CUNY, 695 Park Avenue, New York, NY 10021 |
We would like to report here the current status of our approach towards benzo-13-arylphenalene (1), a molecule well suited for study of paratropic effects associated with planar 4n systems. Benzo-13-(p-tolyl)phenalene is the first 4n system with an aryl group within the p perimeter, allowing a mapping of the ring current effects in it. AM1 calculations have shown that compared to long sought - after 13-methylphenalene (2), benzo-13-phenylphenalene is more stable with a significantly stronger central carbon-carbon bond.Our synthetic approach towards benzo-13-(p-tollyl)phenalene is based on the intramolecular Diels Alder reaction of o-quinodimethane intermediate, obtained by thermolysis of benzcyclobutene derivative. We wish to report the synthesis of dihydro-benzo-13-(p-tolyl)phenalene as well as our results towards the fully conjugated molecule 1. A comparative discussion of our AM1 calculation of 1, 2 and related systems will be included in this presentation.  |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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