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Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones
Przemyslaw Maslak1, Sridhar Varadarajan, Jeffrey D. Burkey
1Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802.
The Journal of Organic Chemistry
|October 25, 2001
Abstract:
Three tetraketones based on the 2,2'-spirobiindan-1,1',3,3'-tetraone skeleton were prepared and investigated. All three compounds show spiroconjugation between their perpendicular pi-networks. The interaction results in lowering of the energy of the LUMO of the systems by ca. 0.2-0.3 eV as compared to non-spiroconjugated models. The spiroketones are susceptible to nucleophile-induced retro-Claisen condensations that lead to molecular rearrangements destroying spiro connectivity.