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[reaction: see text] Compact flow reactors have been constructed and optimized to perform continuous organic photochemistry on a large scale. The reactors were constructed from commercially available or customized immersion well equipment combined with UV-transparent, solvent-resistant fluoropolymer (FEP) tubing. The reactors were assessed using the [2 + 2] photocycloaddition of malemide 1 and 1-hexyne forming the cyclobutene product 2 and the intramolecular [5 + 2] photocycloaddition of 3,4-dimethyl-1-pent-4-enylpyrrole-2,5-dione 3 to form the bicyclic azepine 4. The reactors were shown to be capable of producing >500 g of 2 and 175 g of 4 in a continuous 24 h processing period. Due to the facile control of irradiation time, the continuous flow reactor was also shown to be superior to a batch reactor for performing a problematic photochemical reaction on a larger scale.

Original publication

DOI

10.1021/jo050705p

Type

Journal article

Journal

J Org Chem

Publication Date

16/09/2005

Volume

70

Pages

7558 - 7564