Practical Evaluation of Compact Fluorescent Lamps for Dye-Sensitized Photooxidation Reactions

Kieran P. Stockton; Joseph P. May; Dennis K. Taylor; Ben W. Greatrex

doi:10.1055/s-0033-1340976

Synlett, Table of Contents

Synlett 2014; 25(08): 1168-1172
DOI: 10.1055/s-0033-1340976

letter

Practical Evaluation of Compact Fluorescent Lamps for Dye-Sensitized Photooxidation Reactions

Kieran P. Stockton

^aSchool of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia Fax: +61(0)267735011 Email: ben.greatrex@une.edu.au

,

Joseph P. May

^aSchool of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia Fax: +61(0)267735011 Email: ben.greatrex@une.edu.au

,

Dennis K. Taylor

^bSchool of Agriculture, Food and Wine, University of Adelaide, South Australia, 5065, Australia

,

Ben W. Greatrex*

^aSchool of Science and Technology, University of New England, Armidale, New South Wales, 2351, Australia Fax: +61(0)267735011 Email: ben.greatrex@une.edu.au

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Abstract

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Abstract

Energy-efficient compact fluorescent lamps (CFL) have been evaluated as a light source for the sensitized generation of singlet oxygen used in the oxidation of 1,3-butadienes and furfural derivatives using a range of dyes including rose bengal, methylene blue, and tetraphenylporphyrin. An ambient temperature water jacket was sufficient to cool reaction mixtures due to the low heat output of lamps and the reaction rates using 110 W of CFL were slower but comparable to those obtained using a 500 W tungsten halogen lamp. The conditions were applied to the photooxidation of a series of furan aldehydes and 1,3-butadienes to give products in good yield in 4–96 hours.

Key words

peroxides - photooxidation - photochemistry - pericyclic reaction - oxygenations - sensitizer

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