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

David C. Harrowven*, Mubina Mohamed, Théo P. Gonçalves, Richard J. Whitby, David Bolien, Helen F. Sneddon

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

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).

Original languageEnglish (US)
Pages (from-to)4405-4408
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number18
DOIs
StatePublished - Apr 27 2012

Keywords

  • cyclobutenones
  • density functional calculations
  • photochemistry
  • rearrangements
  • small ring systems

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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