Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

Photochemical and Photobiological Sciences

Volumn 3, Issue 2, 2004, Pages 182-188

  Adam, Waldemar ^a   Kazakov, Dmitri V ^a,b   Kazakov, Valeri P ^b   Kiefer, Wolfgang ^a   Latypova, Ramilya R ^b   Schlücker, Sebastian ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETONE; ANION; BROMINE; CHLORINE; DIMETHYLDIOXIRANE; HYDROGEN; IODINE; METHYL(TRIFLUOROMETHYL)DIOXIRANE; OXIDE; OXIDIZING AGENT; POTASSIUM SALT; SINGLET OXYGEN; SODIUM CHLORIDE; SODIUM HYDROXIDE; THENOYLTRIFLUOROACETONE; UNCLASSIFIED DRUG; WATER;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CHEMOLUMINESCENCE; CONTROLLED STUDY; DECOMPOSITION; INFRARED RADIATION; PHOTOCATALYSIS; PHOTOOXIDATION; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 3042701023     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b311009p     Document Type: Article

References (40)

1. W. Adam C. R. Saha-Müller C. Zhao Dioxirane epoxidation of alkenes Org. React. 2002 61 219-516.
2. V. P. Kazakov A. I. Voloshin D. V. Kazakov Dioxiranes: from oxidative transformations to chemiluminescence Russ. Chem. Rev. 1999 68 253-286.
3. W. Adam, L. P. Hadjiarapoglou, R. Curci and R. Mello, Dioxiranes, 3-Membered ring cyclic peroxides, in Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992, vol. 4, pp. 195–219.
4. W. Adam R. Curci J. O. Edwards Dioxiranes: a new class of powerful oxidants Acc. Chem. Res. 1989 22 205-211.
5. R. W. Murray Dioxiranes Chem. Rev. 1989 89 1187-1201.
6. W. Adam L. Hadjiarapoglou Dioxiranes: Oxidation Chemistry Made Easy Top. Curr. Chem. 1993 164 45-62.
7. W. Adam K. Briviba F. Duschek D. Golsch W. Kiefer H. Sies Formation of singlet oxygen in the deoxygenation of heteroarene N-oxides by dimethyldioxirane J. Chem. Soc., Chem. Commun. 1995 1831-1832.
8. M. Ferrer F. Sanchez-Baeza A. Messeguer W. Adam D. Golsch W. Kiefer V. Nagel The release of singlet oxygen in the reaction of dioxiranes with amine N-oxides Eur. J. Org. Chem. 1998 2527-2532.
9. 2-dimethyldioxirane, in Bioluminescence & Chemiluminescence: Perspectives for the 21st Century, ed. A. Roda, M. Pazzagli, L. J. Kricka and P. E. Stanley, Wiley, Chichester, 1999, pp. 29–32.
10. D. V. Kazakov A. I. Voloshin V. V. Shereshovets V. N. Yakovlev V. P. Kazakov Formation of singlet oxygen in the system tris(bipyridine)ruthenium(II)-dimethyldioxirane Mendeleev Commun. 1998 169-170.
11. D. V. Kazakov G. Ya. Maistrenko N. P. Polyakova R. R. Latypova V. P. Kazakov W. Adam A. V. Trofimov G.-G. Zhao W. Kiefer S. Schlücker On the chemiluminescence in the oxidation of tetravalent uranium to the uranyl ion by dimethyldioxirane Luminescence 2002 17 293-298.
12. A. Lange H.-D. Brauer On the formation of dioxiranes and of singlet oxygen by the ketone-catalysed decomposition of Caro’s acid J. Chem. Soc., Perkin Trans. 2 1996 805-811.
13. A. Lange M. Hild H.-D. Brauer New aspects concerning the mechanism of the ketone-catalysed decomposition of Caro’s acid J. Chem. Soc., Perkin Trans. 2 1999 1343-1350.
14. A. Lange and H.-D. Brauer, Formation of dioxiranes and singlet molecular oxygen by the ketone-catalyzed decomposition of peroxycarboxylic acids, in DFG Research Report on Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer, ed. W. Adam, Wiley-VCH, Weinheim, 2000, pp. 157–162.
15. D. Yang Y. C. Tang J. Chen X. C. Wang M. D. Bartberger K. N. Houk L. Olson Ketone-catalyzed decomposition of peroxynitrite via dioxirane intermediates J. Am. Chem. Soc. 1999 121 11976-11983.
16. V. Nagel F. Duschek W. Kiefer F. Görth D. Golsch W. Adam M. Ferrer A. Messeguer Detection of singlet oxygen during several organic reactions by chemiluminescence spectroscopy Asian J. Spectrosc. 1998 2 35-43.
17. W. Adam, W. Kiefer, S. Schlücker, C. Saha-Möller, D. V. Kazakov, V. P. Kazakov and R. R. Latypova, Formation of singlet oxygen during the decomposition of dimethyldioxirane, catalyzed by anionic nucleophiles, in Bioluminescence & Chemiluminescence: Progress and Current Applications, ed. P. E. Stanley and L. J. Krucka, World Scientific Publishing, Singapore, 2002, pp. 129–32.
18. F. M. Raushel T. O. Baldwin Proposed mechanism of bacterial bioluminescence reaction involving a dioxirane intermediate Biochem. Biophys. Res. Commun. 1989 164 1137-1142.
19. W. A. Francisco H. M. Abu-Soud A. J. DelMonte D. A. Singleton T. O. Baldwin F. M. Raushel Deuterium kinetic isotope effects and the mechanism of the bacterial luciferase reaction Biochemistry 1998 37 2596-2606.
20. G. L. Sharipov, V. P. Kazakov and G. A. Tolstikov, Chemistry and chemiluminescence of 1,2-dioxetanes, Nauka, Moscow, 1990.
21. A. Gordon and R. A. Ford, The chemist’s companion, Wiley, New York, 1972.
22. W. Adam J. Bialas L. Hadjiarapoglou A convenient preparation of acetone solutions of dimethyldioxirane Chem. Ber. 1991 124 2377.
23. W. Adam Y. Y. Chan D. Cremer J. Gauss D. Scheutzow M. Schindler Spectral and chemical properties of dimethyldioxirane as determined by experimental and ab initio calculations J. Org. Chem. 1987 52 2800-2803.
24. W. Adam R. Curci M. E. G. Nunez R. Mello Thermally and photochemically initiated radical chain decomposition of ketone-free methyl(trifluoromethyl)dioxirane J. Am. Chem. Soc. 1991 113 7654-7658.
25. M. Gibert M. Ferrer F. Sanchez-Baeza A. Messeguer Availability and reactivity of concentrated dimethyldioxirane solutions in solvents other than acetone Tetrahedron 1997 53 8643-8650.
26. B. M. Monroe, in Singlet Oxygen, ed. A. A. Frimer, CRC Press, Boca Raton, FL, 1985, vol. 1.
27. g) J. Phys. Chem. 1990 94 4377-4378.
28. g) in solution J. Am. Chem. Soc. 1989 111 6983-6987.
29. g) J. Phys. Chem. 1995 99 3521-3526.
30. T. A. Jenny N. J. Turro Solvent and deuterium isotope effects on the lifetime of singlet oxygen determined by direct emission spectroscopy at 1.27 μm Tetrahedron Lett. 1982 23 2923-2926.
31. W. Adam G. Asensio R. Curci M. E. González-Nánez R. Mello One-electron reduction of methyl(trifluoromethyl)dioxirane by iodide ion. Evidence for an electron-transfer chain reaction mediated by the superoxide ion J. Am. Chem. Soc. 1992 114 8345-8349.
32. M. Ferrer F. Sanchezbaeza J. Casas A. Messeguer Decomposition of dioxiranes induced by dialkyl ethers Tetrahedron Lett. 1994 35 2981-2984.
33. J. Bouchard C. Maine R. M. Berry D. S. Argyropoulos Kraft pulp bleaching using dimethyldioxirane: stability of the oxidants Can. J. Chem. 1996 74 232-237.
34. F. Wilkinson W. P. Helman A. B. Ross Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised complitation J. Phys. Chem. Ref. Data 1995 24 663-1021.
35. Y. L. Fu A. A. Krasnovsky C. S. Foote Singlet oxygen dimol-sensitized luminescence from thermally generated singlet oxygen J. Am. Chem. Soc. 1993 115 10282-10285.
36. P. D. Mascio H. Sies Quantification of singlet oxygen generated by thermolysis of 3,3′-(1,4-naphthylidene)dipropionate-monomol and dimol photoemission and the effects of 1,4-diazabicyclo[2.2.2]octane J. Am. Chem. Soc. 1989 111 2909-2914.
37. A. U. Khan The discovery of the chemical evolution of singlet oxygen. Some current chemical, photochemical, and biological applications Int. J. Quantum Chem. 1991 39 251-267.
38. K. Sakanishi Y. Kato E. Mizukoshi K. Shimizu A novel chemiluminescence from the reaction of 9-arylmethylene-10-methyl-9,10-dihydroacridines and dimethyldioxirane Tetrahedron Lett. 1994 35 4789-4792.
39. D. V. Kazakov A. B. Barzilova V. P. Kazakov A novel chemiluminescnece from the reaction of dioxiranes with alkanes. Proposed mechanism of oxygen-transfer chemiluminescence Chem. Commun. 2001 191-192.
40. D. V. Kazakov G. Ya. Mainstrenko O. A. Kotchneva R. R. Latypova V. P. Kazakov Chemiluminescence in the oxidation of europium β-diketonates by dimethyldioxirane Mendeleev Commun. 2001 188-190.