An Efficient Flow‐Photochemical Synthesis of 5H‐Furanones Leads to an Understanding of Torquoselectivity in Cyclobutenone Rearrangements
An Efficient Flow‐Photochemical Synthesis of 5H‐Furanones Leads to an Understanding of Torquoselectivity in Cyclobutenone Rearrangements
Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates.
cyclobutenone, DFT-rechnungen, kleinringsysteme, photochemie, umlagerungen
4481-4484
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Mohamed, Mubina
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Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Bolien, David
5714a236-3f98-4069-9f96-a920c7a2966c
Sneddon, Helen F.
33850179-8489-433a-b8c9-09536a4e2b18
27 April 2012
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Mohamed, Mubina
f564fdda-ede9-49b8-8689-2e9fe1a90fa8
Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Bolien, David
5714a236-3f98-4069-9f96-a920c7a2966c
Sneddon, Helen F.
33850179-8489-433a-b8c9-09536a4e2b18
Harrowven, David C., Mohamed, Mubina, Gonçalves, Théo P., Whitby, Richard J., Bolien, David and Sneddon, Helen F.
(2012)
An Efficient Flow‐Photochemical Synthesis of 5H‐Furanones Leads to an Understanding of Torquoselectivity in Cyclobutenone Rearrangements.
Angewandte Chemie, 124 (18), .
(doi:10.1002/ange.201200281).
(PMID:22441937)
Abstract
Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates.
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e-pub ahead of print date: 22 March 2012
Published date: 27 April 2012
Keywords:
cyclobutenone, DFT-rechnungen, kleinringsysteme, photochemie, umlagerungen
Identifiers
Local EPrints ID: 337476
URI: http://eprints.soton.ac.uk/id/eprint/337476
ISSN: 0044-8249
PURE UUID: 471fd207-c75b-4bd4-9104-75e9f3e4c081
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Date deposited: 26 Apr 2012 10:52
Last modified: 15 Mar 2024 02:47
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Contributors
Author:
Mubina Mohamed
Author:
Théo P. Gonçalves
Author:
David Bolien
Author:
Helen F. Sneddon
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