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

doi:10.1016/S0040-4039(97)10381-1

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	8663-8666
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(97)10381-1
State	Published - Dec 15 1997

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

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.",

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

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.",

year = "1997",

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doi = "10.1016/S0040-4039(97)10381-1",

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T1 - Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

AU - Muller, Cheryl L.

AU - Bever, Jason R.

AU - Dordel, Mark S.

AU - Kitabwalla, Moiz M.

AU - Reineke, Theresa M.

AU - Sausker, Justin B.

AU - Seehafer, Troy R.

AU - Li, Yu

AU - Jasinski, Jerry P.

N1 - 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.

PY - 1997/12/15

Y1 - 1997/12/15

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4039(97)10381-1

DO - 10.1016/S0040-4039(97)10381-1

M3 - Article

AN - SCOPUS:0030834779

SN - 0040-4039

VL - 38

SP - 8663

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

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

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