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

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

• References


For reviews, see:
• 1a Clennan EL. Tetrahedron 2000; 56: 9151
• 1b Hoffmann N. Chem. Rev. 2008; 108: 1052

For recent applications, see:
• 1c Kouridaki A, Montagnon T, Kalaitzakis D, Vassilikogiannakis G. Org. Biomol. Chem. 2013; 11: 537
• 1d Montagnon T, Tofi M, Vassilikogiannakis G. Acc. Chem. Res. 2008; 41: 1001
• 1e Yong KW. L, Lambert LK, Hayes PY, De Voss JJ, Garson MJ. J. Nat. Prod. 2012; 75: 351
• 2 Prein M, Adam W. Angew. Chem., Int. Ed. Engl. 1996; 35: 477
• 3a Gorman AA, Rodgers MA. J. Chem. Soc. Rev. 1981; 10: 205
• 3b DeRosa MC, Crutchley RJ. Coord. Chem. Rev. 2002; 233: 351
• 4a Clennan EL, Zhang H. J. Am. Chem. Soc. 1995; 117: 4218
• 4b Avery TD, Taylor DK, Tiekink ER. J. Org. Chem. 2000; 65: 5531
• 4c El Mansy MF, Sar A, Lindeman S, Donaldson WA. Chem. Eur. J. 2013; 19: 2330
• 4d Mascal M, Saikat D. Green Chem. 2011; 13: 40
• 5 Vassilikogiannakis G, Margaros I, Montagnon T, Stratakis M. Chem. Eur. J. 2005; 11: 5899
• 6 Li Y.-S, Wang Z.-T, Luo S.-D, Li S.-S, Zhu D.-Y. Nat. Prod. Res. 2006; 20: 724
• 7 Elvidge CD, Keith DM, Tuttle BT, Baugh KE. Sensors 2010; 10: 3961
• 8a Taylor DK, Avery TD, Greatrex BW, Tiekink ER, Macreadie IG, Macreadie PI, Humphries AD, Kalkanidis M, Fox EN, Klonis N. J. Med. Chem. 2004; 47: 1833
• 8b Macreadie IG, Avery TD, Robinson TV, Macreadie P, Barraclough M, Taylor DK, Tiekink ER. Tetrahedron 2008; 64: 1225
• 9 Ogilby PR, Foote CS. J. Am. Chem. Soc. 1983; 105: 3423
• 10 Feldmann C, Jüstel T, Ronda CR, Schmidt PJ. Adv. Funct. Mat. 2003; 13: 511
• 11 Vaske YS. M, Mahoney ME, Konopelski JP, Rogow DL, McDonald WJ. J. Am. Chem. Soc. 2010; 132: 11379
• 12 McDermott S, Walsh J, Howard R. Opt. Laser Technol. 2008; 40: 487
• 13 Lévesque FO, Seeberger PH. Org. Lett. 2011; 13: 5008
• 14 Lamberts J, Neckers D. Tetrahedron 1985; 41: 2183
• 15 Wilkinson F, Helman WP, Ross AB. J. Phys. Chem. Ref. Data 1993; 22: 111
• 16 Wilkinson F, Helman WP, Ross AB. J. Phys. Chem. Ref. Data 1995; 24: 663
• 17 Linden SM, Neckers D. Photochem. Photobiol. 1988; 47: 543
• 18 Gollnick K, Griesbeck A. Tetrahedron 1985; 41: 2057
• 19 Hilt G, Danz M. Synthesis 2008; 2257
• 20 Urkalan KB, Sigman MS. Angew. Chem. 2009; 121: 3192
• 21 O’Shea KE, Foote CS. J. Am. Chem. Soc. 1988; 110: 7167
• 22 Motoyoshiya J, Okuda Y, Matsuoka I, Hayashi S, Takaguchi Y, Aoyama H. J. Org. Chem. 1999; 64: 493