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A Singlet Oxygen Approach to Oxaspirocycles

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Jones,  Kevin Mark
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Hillringhaus,  Tim
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Klussmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Jones, K. M., Hillringhaus, T., & Klussmann, M. (2013). A Singlet Oxygen Approach to Oxaspirocycles. Tetrahedron Letters, 54(25), 3294-3297. doi:10.1016/j.tetlet.2013.04.064.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-A519-9
Abstract
A method for the preparation of oxygen containing spirocycles using singlet oxygen is reported. A series of phenols were converted into the corresponding peroxy-cyclohexadienone derivatives by irradiation with visible light in the presence of a sensitizer and oxygen. The resulting peroxides could be converted into ether and lactone spirocycles in one or two steps. The synthesis of the oxaspirocycles from the phenols can also be performed in a one-pot fashion, avoiding the isolation of the peroxide intermediates.