UVA self-photosensitized oxygenation of β-ionone

Photochemistry and Photobiology

Volumn 83, Issue 6, 2007, Pages 1313-1318

  Borsarelli, Claudio D ^a   Mischne, Mirta ^b   Venia, Agustina La ^b   Vieyra, Faustino E Morán ^a  

^a UNIVERSIDAD NACIONAL DE SANTIAGO DEL ESTERO   (Argentina)

^b Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36248992276     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2007.00147.x     Document Type: Article

References (36)

1. Turro, N. J. (1978) Modern Molecular Photochemistry. Benjamin/Cummings, Menlo Park, CA.
2. g)] in photosensitized oxidation reactions. Acc. Chem. Res. 39, 797 804.
3. Clennan, E. L. A. Pace (2005) Advances in singlet oxygen chemistry. Tetrahedron 61, 6665 6691.
4. Bartoschek, A., T. T. El-Idreesy, A. G. Griesbeck, L.-O. Höinck, J. Lex, C. Miara J. M. Neudörfl (2005) A family of new 1,2,4-trioxanes by photooxygenation of allylic alcohols in sensitizer-doped polymers and secondary reactions. Synthesis 14, 2433 2444.
5. Hakimelahi, G. H., M. L. Jain, T. Wei Ly, I.-C. Chen, K. S. Ethiraj, J. R. Hwu A. A. Moshfegh (2001) Self-sensitized photooxygenation of 3,4-dialkoxyfurans to vitamin C or its derivatives. J. Org. Chem. 66, 7067 7071.
6. Jochkush, S., R. X. Ren, Y. P. Jang, Y. Itagaki, H. R. Vollmer-Snarr, J. R. Sparrow, K. Nakanishi N. J. Turro (2004) Photochemistry of A1E. A retinoid with a pyridinium moiety: Competition between pericyclic photooxygenation and pericyclization. J. Am. Chem. Soc. 126, 4646 4652.
7. Polyakov, N. E., A. I. Kruppa, V. S. Bashurova, R. N. Musin, T. V. Leshina L. D. Kispert (1999) Single electron transfer in the phototransformations of β-ionone in the presence of electron acceptor. J. Photochem. Photobiol. A, Chem. 128, 65 74.
8. Polyakov, N. E., A. I. Kruppa, V. S. Bashurova, T. V. Leshina L. D. Kispert (2002) The role of radicals in the phototransformations of β-ionone in the presence of electron donors in solution. J. Photochem. Photobiol. A, Chem. 153, 113 119.
9. Abarbri, M., J.-L. Parrain, A. Duchêne J. Thibonnet (2006) Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues. Synthesis 17, 2951 2970.
10. 2-catalyzed allylic oxidations of ionone-like dienes. Synlett 16, 2617 2620.
11. Fráter, G., J. A. Bajgrowicz P. Kraft (1998) Fragrance chemistry. Tetrahedron 54, 7633 7703.
12. Huber, S. N. M. P. Mischne (1995) A simple and efficient approach for the synthesis of a 1,2,4-trioxane related to the artemisinin. Nat. Prod. Lett. 7, 43 46.
13. Mischne, M. P., S. N. Huber J. Zinckzuk (1999) Photochemical reaction of β-ionone derivatives in the presence of oxygen. A convenient synthesis of substituted 1,2,4-trioxanes. Can. J. Chem. 77, 237 241.
14. Borsarelli, C. D., S. G. Bertolotti C. M. Previtali (2002) Thermodynamic changes in the photoinduced proton-transfer reaction of the triplet state of safranine-T. Photochem. Photobiol. Sci. 1, 574 580.
15. Rios, A. O., A. Z. Mercadante C. D. Borsarelli (2007) Triplet state energy of the carotenoid bixin determined by photoacoustic calorimetry. Dyes Pigments. 74, 561 565.
16. Montenegro, M. A., I. L. Nunes, A. Z. Mercadante C. D. Borsarelli (2007) Photoprotection of vitamins in skimmed milk by aqueous soluble lycopene - gum arabic microcapsule. J. Agric. Food Chem. 55, 323 329.
17. Mousseron-Canet, M., J.-C. Mani J.-P. Dalle (1967) Photooxydation sensilibiliseé dans la sérié de la β-ionone. Bull. Soc. Chim. 2, 608 612.
18. Büchi, G. N. C. Yang (1957) Light-catalyzed organic reactions. VI. The isomerization of some dienones. J. Am. Chem. Soc., 79, 2318 2323.
19. van Wageningen, A., H. Cerfontain J. A. J. Geenevasen (1975) Photochemistry of non-conjugated dienones. Part V. Photolysis of (E)-β-ionone and its isomeric α-pyran. J. Chem. Soc. Perkin II 12, 1283 1286.
20. Cerfontain, H., J. A. J. Geenevasen P. C. M. van Noort (1980) Photochemistry of dienones. Part 7. On the photosensitized isomerization of (E)-β-ionone and its isomeric α-pyran. Evidence for exciplex formation between the α-pyran and Fluoren-9-one. J. Chem. Soc. Perkin II 7, 1057 1062.
21. Marvell, E. N., G. Caple, T. A. Gosink G. Zimmer (1966) Valence isomerization of a cis-dienone to an α-pyran. J. Am. Chem. Soc. 88, 619 620.
22. Wilkinson, F. J.G. Brummer (1981) Rate constants for the decay and reactions of the lowest electronically excited state of molecular oxygen in solution. J. Phys. Chem. Ref. Data. 10, 809 999.
23. Becker, R. S., R. V. Bensasson, J. Lafferty, T. G. Truscott E. J. Land (1978) Triplet excited states of carbonyl-containing polyenes. J. Chem. Soc. Faraday Trans. 2. 74, 2246 2255.
24. Chattopadhyay, S. K., C. V. Kumar P. K. Das (1985) Triplet excitation transfer involving β-ionone. A kinetic study by laser flash photolysis. Photochem. Photobiol. 42, 17 24.
25. Rudzki, J. E., J. L. Goodman K.S. Peters (1985) Simultaneous determination of photoreaction dynamics and energetics using pulsed, time-resolved photoacoustic calorimetry. J. Am. Chem. Soc. 107, 7849 7854.
26. Nonell, S., C. Martí, I. García-Moreno, A. Costela R. Sastre (2001) Opto-acoustic study of tinuvin-P and rhodamine 6 G in solid polymeric matrices. Appl. Phys. B 72, 355 360.
27. Feiss, A., B. Wegewijs, W. Gärtner S. E. Braslasvky (1997) The role of triplet state in retinal photoisomerisation as studied by laser induced optoacoustic spectroscopy. J. Phys. Chem. 101, 7620 7627.
28. g) photosensitization. Time-resolved photoacoustic and near-IR emission studies. J. Photochem. Photobiol. A, Chem. 97, 11 18.
29. Lambert, C. R. W. Redmond (1994) Triplet energy level of β-carotene. Chem. Phys. Lett. 228, 495 498.
30. Montenegro, M. A., M. A. Nazareno C. D. Borsarelli (2007) Kinetic of the photosensitized oxygenation of the flavanone naringin and its chalcone. J. Photochem. Photobiol. A, Chem. 186, 47 56.
31. Montenegro, M. A., M. A. Nazareno, E. N. Durantini C. D. Borsarelli (2002) Singlet oxygen quenching ability of carotenoids in a reverse micelle membrane mimetic system. Photochem. Photobiol. 75, 353 362.
32. Stratton, S. P., W. H. Schaeffer D. C. Liebler (1993) Isolation and identification of singlet oxygen oxidation products of β-carotene. Chem. Res. Toxicol. 6, 542 547.
33. Baron, M. H., M. J. Coulange, C. Coupry, D. Baron, J. Favrot M. M. Abo Aly (1989) All-trans retinal photoisomerization and photooxidation from UV laser radiation. Vibrational assignment of all-trans 5,8-peroxyretinal. Photochem. Photobiol. 49, 739 743.
34. Etoh, H., K. Ina M. Iguchi (1973) Photosensitized oxygenation of α-pyran derived from β-ionone. Agric. Biol. Chem. 37, 2241 2244.
35. Adam, W. A. G. Griesbeck (1995) Photooxygenation of 1,3-dienes. In CRC Handbook of Organic Photochemistry and Photobiology, Chapter 25 (Edited by W. M. Horspool P.-S. Song pp. 311 324. CRC Press, Boca Raton, FL.
36. Tietze, L. F. (1996) Domino reactions in organic synthesis. Chem. Rev. 96, 115 136.