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Diels–Alder reaction of fused pyran-2-ones with ethyl vinyl ether

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Abstract

Ethyl vinyl ether was found to be an appropriate synthetic equivalent of acetylene for a set of Diels–Alder reactions with fused pyran-2-ones that yield fused carbocyclic systems. Transformations were conducted under microwave irradiation with DABCO (as a catalyst for the elimination of ethanol) and with n-butanol as the additive. A single-crystal X-ray diffraction structure is presented for N-(5,6,7,8-tetrahydro-6-methyl-8-oxonaphthalen-2-yl)benzamide.

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Acknowledgments

We are grateful to the Ministry of Higher Education, Science and Technology of the Republic of Slovenia and the Slovenian Research Agency for financial support (grant nos. P1-0230-0103 and P1-0230-0175). Dr. B. Kralj and Dr. D. Žigon (Center for Mass Spectroscopy, Jožef Stefan Institute, Ljubljana, Slovenia) are gratefully acknowledged for the mass measurements. This work was also partially supported by the infrastructure of the EN–FIST, Center of Excellence, Ljubljana, Slovenia.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000, Ljubljana, Slovenia

    Amadej Juranovič, Krištof Kranjc, Slovenko Polanc, Franc Perdih & Marijan Kočevar

  2. CO EN-FIST, Dunajska cesta 156, 1000, Ljubljana, Slovenia

    Franc Perdih

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  1. Amadej Juranovič
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  2. Krištof Kranjc
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  3. Slovenko Polanc
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  4. Franc Perdih
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  5. Marijan Kočevar
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Correspondence to Franc Perdih or Marijan Kočevar.

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Juranovič, A., Kranjc, K., Polanc, S. et al. Diels–Alder reaction of fused pyran-2-ones with ethyl vinyl ether. Monatsh Chem 143, 771–777 (2012). https://doi.org/10.1007/s00706-012-0734-4

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  • DOI: https://doi.org/10.1007/s00706-012-0734-4

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