Controlled light-induced release of volatile aldehydes and ketones by photofragmentation of 2-oxo-(2-phenyl)acetates

Chimia

Volumn 61, Issue 10, 2007, Pages 661-664

  Levrand, Barbara ^b   Herrmann, Andreas ^a  

^a Analysis and Perception Department   (Switzerland)

^b NONE

Author keywords

Delivery systems; Fragrances; Keto esters; Photooxidations; Triggered release

Indexed keywords

EID: 36048988515     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2007.661     Document Type: Article

References (23)

1. See for example: A. M. Braun, M.-T. Maurette, E. Oliveros, 'Photochemical Technology', J. Wiley & Sons, Chichester, 1991.
2. a) V N. R. Pillai, Synthesis 1980, 1;
3. b) C. G. Bochet, J. Chem. Soc., Perkin Trans. 1 2002, 125;
4. c) A. P. Pelliccioli, J. Wirz, Photochem. Photobiol. Sci. 2002, 1, 441.
5. a) 'Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules', Eds. M. Goeldner, R. Givens, Wiley-VCH, Weinheim, 2005;
6. b) G. Mayer, A. Heckel, Angew. Chem., Int. Ed. 2006, 45, 4900.
7. G. Dormán, G. D. Prestwich, Trends Biotechnol. 2000, 18, 64.
8. A. Herrmann, The Spectrum (Bowling Green) 2004, 17(2), 10-13 and 19 and references cited therein.
9. A. Herrmann, Angew. Chem., Int. Ed. 2007, 46, 5836.
10. a) C. H. Bamford, R. G. W. Norrish, J. Chem. Soc. 1935, 1504;
11. b) J. C. Scaiano, E. A. Lissi, M. V. Encina, Rev. Chem. Intermed. 1978, 2, 139 and standard textbooks of organic photochemistry.
12. a) S. Hu, D. C. Neckers, J. Org. Chem. 1997, 62, 564;
13. b) S. Hu, D. C. Neckers, J. Org. Chem. 1997, 62, 6820.
14. J. Pika, A. Herrmann, C. Vial, to Firmenich SA, WO 99/60990, 1999,
15. Chem. Abstr. 2000, 132, 15499.
16. S. Rochat, C. Minardi, J.-Y. de Saint Laumer, A. Herrmann, Helv. Chim. Acta 2000, 83, 1645.
17. A. Herrmann, C. Debonneville, V. Laubscher, L. Aymard, Flavour Fragr. J. 2000, 15, 415.
18. a) S. Hu, D. C. Neckers, J. Photochem. Photobiol. A, Chem. 1998, 118, 75;
19. b) M. C. Pirrung, R. J. Tepper, J. Org. Chem. 1995, 60, 2461.
20. The synthesis of 6 by transesterification of 2 with geraniol in the presence of dioctyltinoxide turned out to be successful (S. Linder, R. L. Snowden, unpublished results).
21. S. Hu, D. C. Neckers, J. Org. Chem. 1996, 67, 6407.
22. -2. These values were found to be comparable to outdoor sunlight irradiation (60000-100000 lux).
23. B. Levrand, A. Herrmann, Photochem. Photobiol. Sci. 2002, 1, 907.