Dimethyldioxirane oxidation of exocyclic (E,E)-cinnamylideneketones

• Author(s): Lévai, Albert ; Silva, Artur ; Santos, Clementina M.M. ; Cavaleiro, José ; Jeko, József
• Date: 2009
• Persistent ID: http://hdl.handle.net/10198/3921
• Origin: Biblioteca Digital do IPB
• Subject(s): Cinnamylideneketones; Dimethyldioxirane; Epoxides; NMR spectroscopy
• Document Type: Article
• Language: English

Description

http://apps.isiknowledge.com/full_record.do?product=UA&search_mode=GeneralSearch&qid=11&SID=X22NMCKHdF5lcLIJG6o&page=1&doc=1&colname=WOS Exocyclic (E,E)-cinnamylideneketones were oxidized by an excess of isolated dimethyldioxirane (DMDO, in acetone solution) at room temperature, providing diastereomeric mixtures of the α,β:γ,δ-diepoxides. In the case of derivatives bearing an ortho-nitrocinnamylidene moiety, α,β-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.