Journal
TETRAHEDRON
Volume 74, Issue 25, Pages 3107-3112Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.11.048
Keywords
Photo-oxidation; Photochemistry; Cyclopentadiene; Singlet oxygen; Supercritical CO2; Liquid CO2; Continuous flow; Flow chemistry
Categories
Funding
- EPSRC [EP/13013341/1]
- University of Nottingham
- EPSRC [EP/P013341/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/P013341/1] Funding Source: researchfish
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A range of products is reported from the photo-oxidation of cyclopentadiene from photochemically generated singlet oxygen (O-1(2)) using carbon dioxide (CO2) as a solvent and 5,10,15,20-tetralds-(penta-fluorophenyl)porphyrin (TPFPP) as a CO2-soluble photosensitizer. The endo-peroxide intermediate, generated from the reaction with singlet oxygen, is transformed into one of several different products in good yield depending on the conditions applied and by adding different reactors and reagents downstream of the photo-reactor, allowing the reaction products to be switched in one streamlined process. The addition of a thermal reactor facilitated the rearrangement of the endoperoxide to form Z-4,5-epoxy-2-pentanal. Quenching with thiourea yielded the syn-diol, (1R,3S)-cyclopent-4-ene-1,3-diol. Treatment with acid or base afforded furfuryl alcohol and 4-hydroxy-2-cyclopentenone respectively. High productivities for all products were obtained when compared to traditional batch reactions. (C) 2017 Elsevier Ltd. All rights reserved.
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