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
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.
cyclobutenones, density functional calculations, photochemistry, rearrangements, small ring systems
4405-4408
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
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 International Edition, 51 (18), .
(doi:10.1002/anie.201200281).
Abstract
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.
This record has no associated files available for download.
More information
e-pub ahead of print date: 22 March 2012
Published date: 27 April 2012
Keywords:
cyclobutenones, density functional calculations, photochemistry, rearrangements, small ring systems
Organisations:
Chemistry
Identifiers
Local EPrints ID: 337265
URI: http://eprints.soton.ac.uk/id/eprint/337265
ISSN: 1433-7851
PURE UUID: 96091401-0d92-41d0-a71d-f48ec58de339
Catalogue record
Date deposited: 20 Apr 2012 12:11
Last modified: 15 Mar 2024 02:47
Export record
Altmetrics
Contributors
Author:
Mubina Mohamed
Author:
Théo P. Gonçalves
Author:
David Bolien
Author:
Helen F. Sneddon
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
