title: Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones.
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.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802.
authors.forename: Przemyslaw
authors.initials: P
authors.lastname: Maslak
authors.forename: Sridhar
authors.initials: S
authors.lastname: Varadarajan
authors.forename: Jeffrey D.
authors.initials: JD
authors.lastname: Burkey