S. Farhadi et al. / Tetrahedron Letters 47 (2006) 8953–8957
8957
6. Adam, W.; Saha-Moller, C. R.; Ganeshpure, P. A. Chem.
Rev. 2001, 101, 3499–3548.
7. Murahashi, S.-I.; Naota, T.; Hirai, N. J. Org. Chem. 1993,
58, 7318–7319.
8. For a review, see: De Nooy, A. E. J.; Besemer, A. C.; van
Bekkum, H. Synthesis 1996, 1153–1174.
9. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org.
Chem. 1987, 52, 2559–2562; (b) Anelli, P. L.; Biffi, C.;
Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970–
2972; (c) Anelli, P. L.; Montanari, F.; Quici, S. J. Org.
Chem. 1990, 55, 212–219.
10. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.;
Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64,
2564–2566.
11. Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S.
J. Org. Chem. 1990, 55, 462–466.
12. Melvin, F.; McNeill, A.; Henderson, P. J. F.; Herbert, R.
B. Tetrahedron Lett. 1999, 40, 1201–1202.
(25 mL) was added to a Pyrex flask containing a Teflon-
coated stirring bar. To this solution was added iodine
(I2, 0.25 mmol, 63.5 mg). Oxygen was bubbled through,
and the reaction mixture was kept under an oxygen
atmosphere (using an O2 balloon). The mixture was vig-
orously stirred and irradiated with a high pressure
400 W mercury lamp using a cut-off Pyrex filter
(k P 320 nm) at room temperature. The reaction was
monitored by TLC and/or GC and after an appropriate
irradiation time, as shown in Table 3, the irradiation
was stopped. A saturated solution of sodium thiosulfate
was added until the brown colour of the reaction mix-
ture disappeared. The mixture was extracted with
dichloromethane. After evaporation of the solvent, the
products were purified by silica gel plate or column
chromatography with the appropriate solvent. All the
products are known and were characterized by the
13. Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett.
2000, 2, 1173–1175.
14. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L.
J. Org. Chem. 1996, 61, 7452–7454.
1
comparison of melting points and IR, H NMR and/
or MS spectra with those of authentic samples or litera-
ture data.25
15. (a) De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.;
Piancatelli, G. J. Org. Chem. 1997, 62, 6974–6977;
(b) Epp, J. B.; Widlanski, T. S. J. Org. Chem. 1999, 64,
293–295.
Acknowledgement
16. (a) Cella, J. A.; McGrath, J. P.; Kelley, J. A.; El-
Soukkarry, O.; Hilpert, L. J. Org. Chem. 1977, 42, 2077–
2080; (b) Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem.
1993, 58, 4837–4843; (c) Rychnovsky, S. D.; Vaidyana-
than, R. J. Org. Chem. 1999, 64, 310–312.
This research was supported by the Department of
Chemistry, University of Lorestan.
17. (a) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett.
2001, 3, 3041–3043; (b) De Luca, L.; Giacomelli, G.;
Masala, S.; Porcheddu, A. J. Org. Chem. 2003, 68, 4999–
5001.
18. Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285–287.
19. (a) Liu, R.; Liang, X.; Dong, C.; Hu, X. J. Am. Chem. Soc.
2004, 126, 4112–4113; (b) Liu, R.; Dong, C.; Liang, X.;
Wang, X.; Hu, X. J. Org. Chem. 2005, 70, 729–731.
20. Horspool, W. M.; Song, P. S. CRC Handbook of Organic
Photochemistry and Photobiology; CRC Press: Boca
Raton, 1995.
21. Farhadi, S.; Afshari, M.; Maleki, M.; Babazadeh, Z.
Tetrahedron Lett. 2005, 46, 8483–8486.
22. Beebe, T. R.; Hensley, V. L.; Ng, F. W.; Neo, R. A.; Scott,
D. J. J. Org. Chem. 1985, 50, 3015–3016, and references
cited therein.
References and notes
1. (a) Hudlicky, M. Oxidations in Organic Chemistry; ACS:
Washington, DC, 1990; (b) Larock, R. C. Comprehensive
Organic Transformations, 2nd ed.; Wiley-VCH: New
York, 1999.
2. Noyori, R.; Hashigushi, S. Acc. Chem. Res. 1997, 30, 97–
102, and references cited therein.
3. (a) Zhan, B.-Z.; White, M. A.; Sham, T.-K.; Pincock, J.
A.; Doucet, R. J.; Rao, K. V. R.; Robertson, K. N.;
Cameron, T. S. J. Am. Chem. Soc. 2003, 125, 2195–2199;
(b) Ciriminna, R.; Pagliaro, M. Chem. Eur. J. 2003, 9,
5067–5073; (c) Sheldon, R. A.; Arends, I. W. C. E.; ten
Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774–
781; (d) Ji, H.-B.; Wang, L.-F. Chin. J. Chem. 2002, 20,
944–950; (e) Hasan, M.; Musawir, M.; Davey, P. N.;
Kozhevnikov, I. V. J. Mol. Catal. A: Chem. 2002, 180, 77–
84; (f) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani,
K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144–7145;
(g) Sheldon, R. A.; Arends, I. W. C. E.; Dijksman, A.
Catal. Today 2000, 57, 157–166; (h) Lee, M.; Chang, S.
Tetrahedron Lett. 2000, 41, 7507–7510; (i) Bleloch, A.;
Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephart, D. S.;
Thomas, A. W. Chem. Commun. 1999, 1907–1908.
4. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400–
3420, and references cited therein; (b) Steinhoff, B. A.; Fix,
S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766–767;
(c) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M.
A. J. Am. Chem. Soc. 2001, 123, 7188–7189; (d) Peterson,
K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185–3189.
5. (a) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S.
M.; Urch, C. J. Science 1996, 274, 2044–2046; (b) Marko,
I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.;
Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999,
64, 2433–2439; (c) Marko, I. E.; Gautier, A.; Dumeunier,
R.; Doda, K.; Philippart, F.; Brown, S. M.; Urch, C. J.
Angew. Chem., Int. Ed. 2004, 43, 1588–1591.
23. Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann,
M. Advanced Inorganic Chemistry, 6th ed.; Wiley: New
York, 1999, p 564.
24. (a) Cecchetto, A.; Fantana, F.; Minisci, F.; Recupero, F.
Tetrahedron Lett. 2001, 42, 6651–6653; (b) Minisci, F.;
Punta, C.; Recupero, F.; Fantana, F.; Pedulli, G. F. Chem.
Commun. 2002, 688–689; (c) Minisci, F.; Recupero, F.;
Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A: Chem. 2003,
204–205, 63–90; (d) Minisci, F.; Recupero, F.; Cecchetto,
A.; Gambaotti, C.; Punta, C.; Faletti, R.; Paganelli, R.;
Pedulli, G. F. Eur. J. Org. Chem. 2004, 109–119;
(e) Annunziatini, C.; Gerini, M. F.; Lanzalunga, O.;
Lucarini, M. J. Org. Chem. 2004, 69, 3431–3438.
25. (a) Moriarty, R. M.; Hu, H.; Gupta, S. C. Tetrahedron Lett.
1981, 22, 1283–1286; (b) Sorg, G.; Mengel, A.; Jung, G.;
Rademann, J. Angew. Chem., Int. Ed. 2001, 40, 4395–4397;
(c) Mulbaier, M.; Giannis, A. Angew. Chem., Int. Ed. 2001,
40, 4393–4394; (d) Moore, J. D.; Finney, S. N. Org. Lett.
2002, 4, 3001–3003; (e) Reed, N. N.; Delgado, M.;
Hereford, K.; Clapham, B.; Janda, K. D. Bioorg. Med.
Chem. Lett. 2002, 12, 2047–2049; (f) Dictionary of Organic
Compounds, 6th ed.; Chapman-Hall: London, 1996.