Synthesis, structure, and nucleophile-induced rearrangements of spiroketones

Przemyslaw Maslak; Sridhar Varadarajan; Jeffrey D. Burkey

doi:10.1021/jo990867j

Synthesis, structure, and nucleophile-induced rearrangements of spiroketones

Przemyslaw Maslak, Sridhar Varadarajan, Jeffrey D. Burkey

Chemistry

Research output: Contribution to journal › Article › peer-review

26 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 language	English (US)
Pages (from-to)	8201-8209
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	64
Issue number	22
DOIs	https://doi.org/10.1021/jo990867j
State	Published - Oct 29 1999

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo990867j

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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.",

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AU - Varadarajan, Sridhar

AU - Burkey, Jeffrey D.

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Y1 - 1999/10/29

N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

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Synthesis, structure, and nucleophile-induced rearrangements of spiroketones

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