Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

Cheryl L. Muller, Jason R. Bever, Mark S. Dordel, Moiz M. Kitabwalla, Theresa M. Reineke, Justin B. Sausker, Troy R. Seehafer, Yu Li, Jerry P. Jasinski

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Abstract

1,3-Dioxin-4-one photosubstrates were prepared by condensation of alkenones with ketoesters or formyl Meldrum's Acid. The resulting dioxinones contained enone and alkene chromophores, linked through the ketal carbon of the dioxinone ring. The dioxinones were irradiated and die regiochemistry of the photoproducts was established. Substrates with a two carbon tether gave head to head products, while substrates with a three or four carbon tether gave predominantly head to tail products.

Original languageEnglish (US)
Pages (from-to)8663-8666
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number50
DOIs
StatePublished - Dec 15 1997

Bibliographical note

Funding Information:
ACKNOWLEDGMENTS. The authors wish to thank the Petroleum Research Fund (Grant 26605-GB 1, to CLM), Research Corporation (to the UWEC Department of Chemistry), and the National Science Foundation (Grant RUI-8818307) for the creation of the New England Molecular Structure Center at Keene State College.

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