The Oxidation of Fullerene[$C_{60}$] using Several Oxidants under Microwave Irradiation

마이크로파 조건에서 여러가지 산화제를 이용한 풀러렌[$C_{60}$의 산화반응

  • Published : 2005.03.31

Abstract

Synthesis or fullerene oxides[$C_{60}(O)_n$] ($n=1{\sim}4$ or n=1) by fullerene[$C_{60}$] and several oxidants such as 3-chloroperoxy benzoic acid, benzoyl peroxide, trichloroisocyanuric acid, and chromium(VI) oxide took place under microwave irradiation. The reactivity in solid state of fullerene[$C_{60}$] with various oxidants under same microwave rendition increased in order or 3- chloroperoxy benzoic acid > benzoyl peroxide > trichloroisocyanuric acid $\simeq$chromium(VI) oxide. The MALDI-TOF-MS, UV-visible spectra and HPLC analysis confirmed that the products of fullerene oxidation were [$C_{60}(O)_n$] ($n=1{\sim}4$ or n=1).

References

  1. D. Bogdal, M. Lukasiewicz, J. Pielichowski, A. Miciak, Sz. Bednaz.,'Microwave-assisted oxidation of alcohols using $Magtrieve^{TM}$', Tetrahedron, 59, 649 (2003)
  2. L. Perreux, A Loupy, 'A Tentative Rationalization of Microwave Effects in Organic Synthesis According to the Reaction Medium, and Mechanistic Considerations', Tetrahedron, 57, 9199 (2001) https://doi.org/10.1016/S0040-4020(00)00968-6
  3. P. Lidstrorn, J. Tierney, J. Wathey, B. Westman, 'Microwave Assisted Organic Synthesis - A Review' Tetrahedron, 57, 9225 (2001)
  4. N.G. Richard, 'Microwaves in Organic Synthesis', ed. by Andre Loupy, lst ed., p.115, Wiley - VCH Verlag Gmb H & Co.KGaA, Weinheim, 2002
  5. Bailliez, M. Renata. D. Figueiredo, Olesker, J. Cleophax, 'A Practical Large-Scale Access to 1,6-Anhydro--D-hexopyranoses by a Solid-Supported Solvent-Free Microwave Assisted Procedure', Synthesis, 7, 1015 (2003)
  6. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boulet, P. Jacquault, D. Mathe, 'New Solvent-Free Organic Synthesis Using Focused Microwaves', Synthesis, 9, 1213 (1998)
  7. A.K. Bose, B.K. Banik, C. Mathur, D.R. Wagle, M.S. Manhas, 'Polyhydroxy Amino Acid Derivatives via $\beta$-Lactams Using Enantiospecific Approaches and Microwave Techniques', Tetrahedron, 56, 5603 (2000)
  8. M.S. Manhas, B.K. Banik, A. Mathur, .J.E. Vincent, A.K. Bose, 'Vinyl-Lactams as Efficient Synthons. Eco-Friendly Approaches via Microwave Assisted Reactions', Tetrahedron, 56, 5587 (2000)
  9. For reviws on fullerene preparation and chemistry see: R.E. Smalley, 'Self-Assembly of the Fullernes' Ace. Chem. Res., 25 (1992)
  10. Special Issue on Buckminster fullerenes Published by the American Chemical Society;. G. S. Hammond, V. J. Kuck, 'Fullerenes: Synthesis, Properities and Chemistry of Large Carbon Clusters', G. S. Hammond, V. J. Kuck, Eds., ACS Symposium Series 481; American Chemical Society: Washington, CD, 1992.
  11. R. Taylor, D. R. M. Walton, 'The Chemistry of Fullerenes' Nature., 363, 685 (1993)
  12. J. M. Wood, B. Kahr, S. H. Hake II., 'Oxygen and Methylene Adducts of $C_{60}$ and $C_{70}$', J. Am. Chem. Soc. 113, 5907 (1991) https://doi.org/10.1021/ja00003a037
  13. K. M. Creegan, W. K. Robbins, J. M. Millar., 'Chroamtographic Separations of Fullerene: discovery and characterization', J. Am. Chem. Soc., 114, 1103 (1992)
  14. J. M. Millar, K. M. Creegan, J. L. Robbins., 'Synthesis and characterization of $C_{60}O$, the First Fullerene Epoxide', Synth. Met. 59,317 (1993)
  15. W.A. Kalsbeck and H.H. Thorp, 'Electrochmical Reduction of Fullerenes in the Presence of $O_2$ and $H_2O$: Polyoxygen Adducts and Fragmentation of the $C_{60}$ Framework', J. Electroanal. Chem., 314, 363 (1991)
  16. Y. Elemes, S. K. Silverman, C. Sheu., 'Resction of $C_{60}$ with Dimethyldioxirane Formation of an Epoxide and a 1,3-Dioxolane Derivative', Aengew. Chem. Int. Ed. Engl., 31, 351 (1992) https://doi.org/10.1002/anie.199203511
  17. D. Heymann and L. P. F. Chibante, 'Phototransformations of $C_{60}$, $C_{70}$, $C_{60}O_2$, and $C_{60}O_2$', Chem. Phys. Lett., 207, 339 (1993)
  18. F. Cataldo and D. Heymann, 'Effects of intense Ultrasound Treatment of $C_{60}$ Solutions', Fullerene Sci. Technol., 7, 725 (1999)
  19. W.B. Ko, J.H. Ahn, Y.A Lim, J..Y. Han, D.S. Han, 'Synthesis of Fullerene Oxides $[C_{70}O_n]$ (n=1-3 or n=1) under Microwave irradiation', Elastomer, 39 (4), 309 (2004)
  20. J.P. Deng, C.Y Mou, C.C. Han, 'Oxidation of Fullerenes by Ozone.' Fullerene Sci.Technol, 5, 1033 (1997)