Dimethyldioxirane Oxidation of Exocyclic (E,E)-Cinnamylideneketones*

Albert Lévai; Artur M. S. Silva; Clementina M. M. Santos; José A. S. Cavaleiro; József Jekő

doi:10.1071/CH08216

RESEARCH ARTICLE

Dimethyldioxirane Oxidation of Exocyclic (E,E)-Cinnamylideneketones*

Albert Lévai ^A ^E , Artur M. S. Silva ^B ^E , Clementina M. M. Santos ^B ^C , José A. S. Cavaleiro ^B and József Jekő ^D

+ Author Affiliations

- Author Affiliations

^A Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary.

^B Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal.

^C Department of Vegetal Production and Technology, Escola Superior Agrária de Bragança, Campus de Santa Apolónia, 5301-855 Bragança, Portugal.

^D Department of Chemistry, College of Nyíregyháza, Sóstói u. 31/b, H-4400 Nyíregyháza, Hungary.

^E Corresponding authors. Email: alevai@puma.unideb.hu; artur.silva@ua.pt

Australian Journal of Chemistry 62(1) 82-89 https://doi.org/10.1071/CH08216
Submitted: 21 May 2008 Accepted: 10 December 2008 Published: 21 January 2009

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 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.

^* Dedicated to Professor Dr Branko Stanovnik on the occasion of his 70th birthday.

Acknowledgements

Thanks are due to the Hungarian Scientific Research Fund (Grant no. T049468) and also to the University of Aveiro, ‘Fundação para a Ciência e a Tecnologia’ and FEDER for funding the Organic Chemistry Research Unit. The technical assistance of Mrs M. Nagy and Mr L. Szabó is highly appreciated.

References

Dimethyldioxirane Oxidation of Exocyclic (E,E)-Cinnamylideneketones*

Abstract

Acknowledgements

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