Singlet oxygen is a powerful reactant in organic synthesis. Its physical properties differ only subtly from those of the more common triplet form of oxygen. Yet in terms of its chemical reactivity, singlet oxygen is far more reactive toward organic compounds. The generation of singlet oxygen and its reaction with organic compounds within a continuous flow photochemical reactor is safer than in traditional batch reactors. In addition, reaction parameters under continuous flow conditions can be precisely controlled to maximize the yield of the desired product.
This application note demonstrates the use of singlet oxygen in flow, investigating a range of parameters that can affect the conversion and throughput. This manuscript focuses on the ene like reaction of singlet oxygen with citronellol and forms the first in a series of technical notes exploring signlet oxygen reactions using the Vapourtec UV-150 reactor in combination with the versatile E-Series flow chemistry system.
The highlights of this application note are:
The Vapourtec E-Series system accurately meters the oxygen and deliver the reagents
The optimal concentration of chosen photosensitizer, Tetraphenylporphyrin (TPP) was found to be low, just 1:1600 molar concentration of TPP to starting material
The optimised throughput was >15 gram / hour using only a single 60 Watt LED lamp
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