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An efficient flow-photochemical synthesis of 5H-furanones leads to an understanding of torquoselectivity in cyclobutenone rearrangements

Record type: Article

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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Citation

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

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 Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 20 Apr 2012 12:11
Last modified: 18 Jul 2017 06:04

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Contributors

Author: Mubina Mohamed
Author: Théo P. Gonçalves
Author: David Bolien
Author: Helen F. Sneddon

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