Continuous-Flow Photochemical Transformations of 1,4-Naphthoquinones and Phthalimides in a Concentrating Solar Trough Reactor
Madyan A. Yaseen A , Saira Mumtaz A , Richard L. Hunter A , Daniel Wall A , Mark J. Robertson A and Michael Oelgemöller A B CA College of Science and Engineering, James Cook University, Townsville, Qld 4811, Australia.
B Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Gent, Belgium.
C Corresponding author. Email: michael.oelgemoeller@jcu.edu.au
Australian Journal of Chemistry 73(12) 1149-1157 https://doi.org/10.1071/CH20138
Submitted: 28 April 2020 Accepted: 15 June 2020 Published: 7 July 2020
Abstract
A series of photochemical transformations has been successfully conducted under continuous-flow conditions in a concentrating solar trough reactor. Photoacylations and [2+2]-photocycloadditions involving 1,4-naphthoquinones gave the corresponding photoproducts in moderate to high yields with residence times of 70 min. Likewise, acetone-sensitized photodecarboxylations involving phthalimides furnished the corresponding benzylated hydroxy phthalimidines in good to excellent yields and purity with residence times of 40 min. Compared with corresponding exposures to direct sunlight conducted in a solar float, flow operation generally gave superior conversions and subsequent yields.
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