Photodecarbonylation of 1,3-dithiophenyl propanone: Using nanocrystals to overcome the filtering effect of highly absorbing trace impurities

Organic Letters

Volumn 9, Issue 21, 2007, Pages 4351-4354

  Resendiz, Marino J E ^a   Taing, Jennifer ^a   Garcia Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35548950394     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702000s     Document Type: Article

References (45)

1. For leading reviews, please see: (a) Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.
2. (b) Sakamoto, M. Chem.-Eur. J. 1997, 3, 684.
3. (c) Scheffer, J. R.; Garcia-Garibay, M. A.; Nalamasu, O. Org. Photochem. 1987, 8, 249.
4. (a) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 122, 7817.
5. (b) Friscic, T.; MacGillivray, L. R. Z Kristallogr. 2005, 220, 351.
6. (c) MacGillivray, L. R.; Papaefstathiou, G. S.; Friscic, T.; Varshney, D. B.; Hamilton, T. D. Top. Curr. Chem. 2004, 248, 201.
7. (d) Amirsakis, D. G.; Garcia-Garibay, M. A.; Rowan, S. J.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2001, 40, 4256.
8. (e) Amirsakis, D. G.; Elizarov, A. M.; Garcia-Garibay, M. A.; Glink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2003, 42, 1126.
9. (a) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem Res. 1996, 29, 203.
10. (b) Scheffer, J. R.; Xia, W. Top. Curr. Chem. 2005, 254, 233.
11. (a) Garcia-Garibay, M. A.; Shin, S. H.; Sanrame, G Tetrahedron 2000, 56, 6729.
12. (b) Garcia-Garibay, M. A. Acc. Chem. Res. 2003, 36, 491.
13. (c) Campos, L. M.; Garcia-Garibay, M. A. In Reviews of Reactive Intermediate Chemistry; Platz, M. S., Jones, M., Moss, R., Eds.; John Wiley and Sons: Hoboken, NJ, 2007.
14. (a) Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 1998.
15. (b) Clark, J. H. Green Chem. 1999, 1, 1.
16. (c) Hölscher, M. Green Chem. 2004, 6, G31.
17. (a) Choi, T.; Peterfy, K.; Khan, S. I.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 2477.
18. (b) Peterfy, K.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1998, 120, 4540.
19. (c) Yang, Z.; Garcia-Garibay, M. A. Org. Lett. 2000, 2, 1963.
20. (d) Yang, Z.; Ng, D.; Garcia-Garibay, M. A. J. Org. Chem. 2001, 66, 4468.
21. (e) Campos, L. M.; Ng, D.; Yang, Z.; Dang, H.; Martinez, H. L.; Garcia-Garibay, M. A. J. Org. Chem. 2002, 67, 3749.
22. (f) Ellison, M. E.; Ng, D.; Dang, H.; Garcia-Garibay, M. A. Org. Lett. 2003, 15, 2531.
23. (g) Choe, T.; Khan, S. I.; Garcia-Garibay, M. A. Photochem. Photobiol. Sci. 2006, 5, 449.
24. Campos, L. M.; Garcia-Garibay, M. A. In CRC Handbook of Organic Photochemistry; Horspool, W. M., Ed.; CRC Press: Boca Raton, FL, 2003.
25. Resendiz, M. J. E.; Garcia-Garibay, M. A. Org. Lett. 2005, 7, 371.
26. Ng, D.; Yang, Z.; Garcia-Garibay. M. A. Org. Lett. 2004, 6, 645.
27. Natarajan, A.; Ng, D.; Yang, Z.; Garcia-Garibay, M. A. Angew. Chem., Int. Ed. 2007, 46, 6485.
28. Mortko, C. J.; Garcia-Garibay, M. A. Top. Stereochem. 2006, 25, 205.
29. (a) Adam, W.; van Barneveld, C.; Emmert, O.; Harrer, H. M.; Kita, F.; Kumar, A. S.; Maas, W.; Nau, W. M.; Reddy, S. H. K.; Wirz, J. Pure Appl. Chem. 1997, 69, 735.
30. (b) Adam, W.; Emmert, O.; Harrer, H. M. J. Chem. Soc., Perkin Trans. 2 1997, 687.
31. Zhao, S.-W.; Liu, L.; Fu, Y.; Guo, Q.-X. J. Phys. Org, Chem. 2005, 18, 353.
32. Sauriat-Dorizon, H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2003, 68, 240.
33. Millard, A. A.; Rathke, M. W. J. Org. Chem. 1978, 43, 1834.
34. Please see Supporting Information for more details.
35. (a) Wiberg, K. B.; Murcko, M. A. J. Comput. Chem. 1988, 9, 488.
36. (b) Wiberg, K. B.; Martin, E. J. Am. Chem. Soc. 1985, 107, 5035.
37. Braverman, S.; Duar, Y.; Freund, M. Isr. J. Chem. 1985, 26, 108.
38. The temperature dependence can be attributed to the existence of energy barriers in the excited state hypersurface. Please see ref 7 and references therein.
39. Keating, A.E.; Garcia-Garibay, M. A. In Organic and Inorganic Photochemistry; Ramamurthy, V., Schanze, K., Eds.; Marcel Dekker: New York, 1998; Vol. 2; pp 195-248 and references therein.
40. (a) Takashi, S.; Miura, H.; Kasai, H.; Okada, H.; Oikawa, H.; Nakanishi, H. J. Am. Chem. Soc. 2002, 124, 10944.
41. (b) Bucar, D.-K.; MacGillivray, L. R. J. Am. Chem. Soc. 2007, 129, 32.
42. (c) Al-Kaysi, R. O.; Bardeen, C. J. Adv. Mater. 2007, 19, 1276.
43. Veerman, M.; Resendiz, M. J. E.; Garcia-Garibay, M. A.:Org. Lett. 2006, 5, 2615.
44. Chin, K. K.; Natarajan, A.; Campos, L. M.; Johansen, E.; Shepherd, H.; Garcia-Garibay, M. A. Chem. Commun. 2007, published online Aug 9, 2007.
45. 2O (10 mL). The excess acetone was removed with a stream of air. The milky-white suspension was placed in a Pyrex container at a distance (∼10 cm) from a mediumpressure Hg Hanovia lamp and stirred while keeping a constant temperature inside the photolysis chamber (ca 25°C). The critical micelle concentration of SDS (cmc = 7-10 mM) was taken from the "Detergent Properties and Application" table from Aldrich; www.sigmaaldrich.com/img/assets/15402/Detergent_Selection_Table.pdf (accessed August 8, 2008).