Singlet oxygen generation from poly[4-diacetoxyiodo]styrene and hydrogen peroxide

Singlet oxygen generation from poly[4-diacetoxyiodo]styrene and hydrogen peroxide

Treatment of hydrogen peroxide with a polymer-supported hypervalent iodine compound, poly[4-diacetoxyiodo] styrene (PDAIS), generates singlet molecular oxygen ( 1 O2). Singlet oxygen generation was proved by trapping with typical organic compounds such as conjugated dienes, aromatic dienes, and electron-rich alkene. When compared to monomer analogue, the use of PDAIS in peroxidation of substrates gave slightly better yields (45% 96%). Regeneration and reuse of PDAIS showed similar activity. The mechanism underlying generation of singlet oxygen and reaction scope was examined.

___

  • 1. Wasserman, H. H.; Ives, J. L. Tetrahedron 1981, 37, 1825-1852.
  • 2. Prein, M.; Adam, W. Angew. Chem. Int. Ed. Eng. 1996, 35, 447-494.
  • 3. Ogilby, P. R. Chem. Soc. Rev. 2010, 39, 3181-3209.
  • 4. Picard, S.; Clermont, G.; Genin, E.; Blanchard-Desce, M. Tetrahedron 2015, 71, 1088-1094.
  • 5. Pedersen, S. K.; Holmehave, J.; Blaikie, F. H.; Gollmer, A.; Breitenbach, T.; Jensen, H. H.; Ogilby, P. R. J. Org. Chem. 2014, 79, 3079-3807.
  • 6. Oleinick, N. L.; Morris, R. L.; Belichenko. T. Photochem. Photobiol. Sci. 2002, 1, 1-21.
  • 7. Dougherty, T. J. J. Clin. Laser Med. Surg. 2002, 20, 3-7.
  • 8. Triesscheijn, M.; Baas, P.; Schellens, J. H. M.; Stewart, F. A. Oncologist 2006, 11, 1034-1044.
  • 9. Ozlem, S.; Akkaya, E. U. J. Am. Chem. Soc. 2009, 131, 48-49.
  • 10. Midden, W. R.; Wang, S. Y. J. Am. Chem. Soc. 1983, 105, 4129-4135.
  • 11. Nowakowska, M.; Sustar, E.; Guillet, J. E. J. Photochem. Photobiol. A 1994, 80, 369-376.
  • 12. Aubry, J. M. J. Am. Chem. Soc. 1985, 107, 5844-5849.
  • 13. Nardello, V.; Marko, J.; Vermeersch, G.; Aubry, J. M. Inorg. Chem. 1995, 34, 4950.
  • 14. Aubry, J. M.; Cazin, B. Inorg. Chem. 1988, 27, 2013-2014.
  • 15. Clague, M. J.; Butler, A. J. Am. Chem. Soc. 1995, 117, 3475-3484.
  • 16. Caron, L.; Nardello, V.; Alsters, P. L.; Aubry, J. M. J. Mol. Catal. A-Chem. 2006, 251, 194-199.
  • 17. Nardello, V.; Bouttemy, S.; Aubry, J. M. J. Mol. Catal. A-Chem. 1997, 117, 439-447.
  • 18. Aubry, J. M.; Cazin, B.; Duprat, F. J. Org. Chem. 1989, 54, 726-728.
  • 19. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358.
  • 20. Moriarty, R. M. J. Org. Chem. 2005, 70, 2893-2903.
  • 21. Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, 9, 26-58.
  • 22. Richardson, R. D.; Wirth, T. Angew. Chem. Int. Ed. 2006, 45, 4402-4404.
  • 23. Yusubov, M. S.; Funk, T. V.; Chi, K. W.; Cha, E. H. Kim, G. H.; Kirschning, A.; Zhdankin, V. V. J. Org. Chem. 2008, 73, 295-297.
  • 24. Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew. Chem. Int. Ed. 2000, 39, 1306-1307.
  • 25. Tohma, H.; Maegawa, T.; Kita, Y. Synlett 2003, 723-725.
  • 26. Sakuratani, K.; Togo, H. ARKIVOC 2003, 6, 11-20.
  • 27. Shang, Y.; But, T. Y. S.; Togo, H.; Toy, P. H. Synlett 2007, 67-70.
  • 28. Jang, H. S.; Chung, W. J.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 3731-3734.
  • 29. Ley, S. V.; Thomas, A. W.; Finch, H. J Chem. Soc. Perk. T. 1 1999, 669-671.
  • 30. Togo, H.; Sakuratani, K. Synlett 2002, 1966-1975.
  • 31. Liu, X. L.; Lin, S. Y.; Sheng, S. R.; Wei, M. H.; Gong, B. J. Chin. Chem. Soc. 2007, 54, 1119-1122.
  • 32. Abe, S; Sakuratani, K; Togo, H. J. Org. Chem. 2001, 66, 6174-6177.
  • 33. Kalberer, E. W.; Whitfield, S. R.; Sanford, M. S. J. Mol. Catal. A-Chem. 2006, 251, 108-113.
  • 34. Catir, M.; Kilic, H. Synlett 2003, 1180-1182.
  • 35. Catir, M.; Kilic, H.; Nardello-Rataj, V.; Aubry, J. M.; Kazaz, C. J. Org. Chem. 2009, 74, 4560-4564.
  • 36. Kalay, E.; Kilic, H.; Catir, M.; Cakici, M.; Kazaz, C. Pure Appl. Chem. 2014, 86, 945-952.
  • 37. Togo, H.; Nogami, G.; Yokoyama, M. Synlett 1998, 534-536.
  • 38. Huang, X.; Zhu, Q. Synth. Commun. 2001, 31, 111-115.
  • 39. Zhang, K.; Kopetzki, D.; Seeberger, P. H.; Antonietti, M.; Vilela, F. Angew. Chem. Int. Ed. 2013, 52, 1432-1436.
  • 40. Paddock, V. L.; Phipps, R. J.; Conde-Angulo, A.; Blanco-Martin, A.; Giro-Manas, C.; Martin, L. J.; White, A. J. P.; Spivey, A. C. J. Org. Chem. 2011, 76, 1483-1486.
  • 41. Pearson, A. J.; Lai, Y. S.; Lu, W. Y.; Pinkerton, A. A. J. Org. Chem. 1989, 54, 3882-3893.
  • 42. Donkers, R. L.; Workentin, M. S. J. Am. Chem. Soc. 2004, 126, 1688-1698.
  • 43. Nandakumar, M.; Sivasakthikumaran, R.; Mohanakrishnan, A. K. Eur. J. Org. Chem. 2012, 3647-3657.
  • 44. Dang, H. S.; Davies, A. G.; Davison, I. G. E.; Schiesser, C. H. J. Org. Chem. 1990, 55, 1432-1438.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

SEID-ALI MIRMIRAN-YAZDI, AFSHIN YAZDANI ELAH ABADI, NASIM SHAMS, RAZIEH MOHEBAT

Ultrasonic activation of the arylation reaction of styrene catalyzed by transition metals

Dhiab ATOUI, Khemais SAİD, Ridha BEN SALEM

Decolorization of reactive orange 16 via ferrate(VI) oxidation assisted by sonication

Serkan ŞAHİNKAYA

Singlet oxygen generation from poly[4-diacetoxyiodo]styrene and hydrogen peroxide

Mustafa ÇATIR

Online coupling electrochemical preconcentration and GFAAS technique as effective method for determination of ultratrace concentrations of antimony in groundwater and surface water samples

Lubomir MACHYNAK, Martin NEMECEK, Ernest BEINROHR, Frantisek CACHO

Synthesis of neodymium-iron nanoperovskite for sensing applications of an antiallergic drug

Nada F. ATTA, Ahmed GALAL, Mohammad H. BINSABT, Ekram H. EL-ADS

The reactions of N33P33Cl66 with monodentate and bidentate ligands: the syntheses and structural characterizations, in vitro antimicrobial activities, and DNA interactions of 4-fluorobenzyl(N/O)spirocyclotriphosphazenes

Aytuğ OKUMUŞ, Gamze ELMAS, Nagehan RAMAZANOĞLU, Zeynel KILIÇ, Mustafa TÜRK, Leyla AÇIK

Yassine El MAATAOUİ, Mohamadine El M'RABET, Abdelkrim MAAROUFI, Hassan OUDDA, Abdelmalek DAHCHOUR

A rapid, efficient, and green synthesis of benzo[$a$]chromeno[2,3-$c$]phenazine derivatives via microwave assistance and DABCO~catalyzed a novel domino cyclization

SEID-ALI MIRMIRAN-YAZDI, AFSHIN YAZDANI ELAH ABADI, NASIM SHAMS, RAZIEH MOHEBAT

LUBOMIR MACHYNAK, MARTIN NEMECEK, ERNEST BEINROHR, FRANTISEK CACHO