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


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).

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Description/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.

Item Type: Article
ISSNs: 1433-7851 (print)
1521-3773 (electronic)
Keywords: cyclobutenones, density functional calculations, photochemistry, rearrangements, small ring systems
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural and Environmental Sciences > Chemistry
ePrint ID: 337265
Date Deposited: 20 Apr 2012 12:11
Last Modified: 14 Apr 2014 11:39
Projects:
Reagent-Free Flow Chemistry: The Generation and Trapping of Reactive Intermediates
Funded by: EPSRC (EP/G027986/1)
Led by: Richard John Whitby
1 October 2009 to 30 September 2013
URI: http://eprints.soton.ac.uk/id/eprint/337265

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