252190-33-3Relevant academic research and scientific papers
Synthesis, structure, and nucleophile-induced rearrangements of spiroketones
Maslak, Przemyslaw,Varadarajan, Sridhar,Burkey, Jeffrey D.
, p. 8201 - 8209 (2007/10/03)
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 π-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.
