Synthesis, structure, and nucleophile-induced rearrangements of spiroketones

Przemyslaw Maslak, Sridhar Varadarajan, Jeffrey D. Burkey

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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 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.

Original languageEnglish (US)
Pages (from-to)8201-8209
Number of pages9
JournalJournal of Organic Chemistry
Volume64
Issue number22
DOIs
StatePublished - Oct 29 1999

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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