PAPER
Efficient and Recyclable Phthalocyanine-Based Sensitizers for Photooxygenation Reactions
1795
UV/Vis (THF): lmax (log e) = 357 (4.98), 608 (4.59), 645 (4.54),
M. R.; Buonerba, G. J. Org. Chem. 2005, 70, 6503.
674 nm (5.40).
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Photooxygenation Reactions: General Procedure
All of the reactions were carried out in a test tube with an oxygen-
inlet apparatus at 0 °C. The concentration of all the substrates was
fixed at 0.1 M with 0.1–0.3 mol% of the sensitizers. A mixture
(CHCl3–MeOH, 9:1) was used as the solvent unless otherwise stat-
ed. The mixtures were stirred with the bubbling of oxygen and were
irradiated with a halogen lamp (250 W or 500 W) placed at ca. 10
cm from the reactor. A glass filter was used to cut off the light (λ <
610 nm) unless otherwise stated. The reactions were monitored by
TLC. The isolated yields and conversions were based on the starting
material and product isolated by column chromatography. The
NMR yields and conversions were determined with reference to the
signals of the products28,29,31 using 2,5-dimethylfuran as an internal
standard.
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Recycling of Sensitizers: General Procedure
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To a solution of 6 (60 mg, 0.54 mmol) or 7 (0.11 mL, 0.68 mmol)
in CHCl3–MeOH (9:1) was added the sensitizer 2, 3, or 5 (0.1–0.3
mol%). The concentration of the substrate was fixed at 0.1 M. The
reaction was monitored by TLC. After all the starting material had
been consumed, an appropriate amount of MeOH was added to in-
duce precipitation of the sensitizer. The recovered sensitizer was
collected by filtration and used in another run of photooxygenation.
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Acknowledgment
This work was supported by a direct grant (2004–05) and a strategic
investments scheme administered by The Chinese University of
Hong Kong.
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Synthesis 2009, No. 11, 1791–1796 © Thieme Stuttgart · New York