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Prof. David C. Harrowven, Mubina Mohamed, Théo P. Gonçalves, Prof. Richard J. Whitby, David Bolien and Dr. Helen F. Sneddon An Efficient Flow-Photochemical Synthesis of 5H-Furanones Leads to an Understanding of Torquoselectivity in Cyclobutenone Rearrangements Angewandte Chemie International Edition 51

Version of Record online: 22 MAR 2012 | DOI: 10.1002/anie.201200281

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Go with the flow: 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 (see scheme).

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