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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
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
1433-7851
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
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), 4405-4408. (doi:10.1002/anie.201200281).

Record type: Article

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.

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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
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 20 Apr 2012 12:11
Last modified: 18 Feb 2021 16:43

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