Journal
CHEMPHOTOCHEM
Volume 3, Issue 5, Pages 229-232Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cptc.201900017
Keywords
Cyclobutene; electrocyclic reactions; flow photochemistry; reactor fouling; UV photochemistry
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Funding
- Austrian COMET Program by the Austrian Federal Ministry of Transport, Innovation and Technology (BMVIT) [862766]
- Austrian Federal Ministry of Science, Research and Economy (BMWFW) [862766]
- State of Styria (Styrian Funding Agency SFG) [862766]
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Cyclobutene lactones hold great potential as synthetic building blocks, yet their preparation by photochemical rearrangement in batch can often be a bottleneck in synthetic studies. We report the use of flow photochemistry as a tool to enable a higher-throughput approach to the synthesis of 2-oxabicyclo[2.2.0]hex-5-en-3-one, which reduces reaction times from 24h to 10min. Accordingly, a significantly improved throughput of 144mg/h (vs 14-21mg/h in batch) was achieved. Scale-out experiments showed problematic reactor fouling and steps were taken to explore and minimize this effect.
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