Dimethyldioxirane oxidation of exocyclic (E,E)-cinnamylideneketones

Albert Ĺvai, Artur M.S. Silva, Clementina M.M. Santos, Joś A.S. Cavaleiro, Jzsef Jek

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Abstract

Exocyclic (E,E)-cinnamylideneketones were oxidized by an excess of isolated dimethyldioxirane (DMDO, in acetone solution) at room temperature, providing diastereomeric mixtures of the ,:,-diepoxides. In the case of derivatives bearing an ortho-nitrocinnamylidene moiety, ,-monoepoxides were also isolated as minor products. The structures of all new compounds and the stereochemistry of the monoepoxides and diepoxide diastereomers were established by NMR studies.

Original languageEnglish
Pages (from-to)82-89
Number of pages8
JournalAustralian Journal of Chemistry
Volume62
Issue number1
DOIs
Publication statusPublished - Feb 4 2009

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ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ĺvai, A., Silva, A. M. S., Santos, C. M. M., Cavaleiro, J. A. S., & Jek, J. (2009). Dimethyldioxirane oxidation of exocyclic (E,E)-cinnamylideneketones. Australian Journal of Chemistry, 62(1), 82-89. https://doi.org/10.1071/CH08216