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), pp. 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
Digital Object Identifier (DOI): doi:10.1002/anie.201200281
ISSNs: 1433-7851 (print)
Keywords: cyclobutenones, density functional calculations, photochemistry, rearrangements, small ring systems
Subjects:
Organisations: Chemistry
ePrint ID: 337265
Date :
Date Event
22 March 2012e-pub ahead of print
27 April 2012Published
Date Deposited: 20 Apr 2012 12:11
Last Modified: 17 Apr 2017 17:17
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/337265

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