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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 4
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Original Articles

Solvent-Free Synthesis of N-Arylfulleropyrrolidine Derivatives Without Using Phase-Transfer Catalyst Under Microwave Irradiation

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Pages 580-586 | Received 19 Dec 2008, Published online: 03 Feb 2010

REFERENCES

  • Taylor , R. ; Walton , D. R. M. The chemistry of fullerenes . Nature 1993 , 363 , 685 – 693 .
  • Hirsch , A. The Chemistry of the Fullerenes ; Thieme : Stuttgart , 1994 .
  • Diederich , F. ; Thilgen , C. Covalent fullerene chemistry . Science 1996 , 271 , 317 – 324 .
  • Thilgen , C. ; Diederich , F. The higher fullerenes: Covalent chemistry and chirality . Top. Curr. Chem. 1999 , 199 , 135 – 171 .
  • Nakamura , E. ; Isobe , H. Functionalized fullerenes in water: The first 10 years of their chemistry, biology, and nanoscience . Acc. Chem. Res. 2003 , 36 , 807 – 815 .
  • Nierengarten , J. F. ; Martin , N. ; Fowler , P. Fullerene Chemistry ; Elsevier SAS : Paris , 2006 .
  • Nazario , M. ; Margarita , A. ; Salvatore , F. ; Angel , M. D. New reactions in fullerene chemistry . Synlett 2007 , 20 , 3077 – 3095 .
  • Prato , M. Fullerene materials . Top. Curr. Chem. 1999 , 199 , 173 – 187 .
  • Yurovskaya , M. A. ; Trushkov , I. V. Cycloaddition to buckminsterfullerene C60: Advancements and future prospects . Russ. Chem. Bull. Int. Ed. 2002 , 51 , 367 – 443 .
  • Peng , R. F. ; Wang , G. W. ; Shen , Y. B. ; Li , Y. J. ; Zhang , T. H. ; Liu , Y. C. ; Murata , Y. ; Komatsu , K. Solvent-free reactions of fullerenes with diethyl bromomalonate in the presence of inorganic bases under high-speed vibration milling conditions . Synth. Commun. 2004 , 34 , 2117 – 2126 .
  • Cardona , C. M. ; Kitaygorodskiy , A. ; Ortiz , A. ; Herranz , M. A. ; Echegoyen , L. The first fulleropyrrolidine derivative of Sc3N@C80: Pronounced chemical shift differences of the geminal protons on the pyrrolidine ring . J. Org. Chem. 2005 , 70 , 5092 – 5097 .
  • Quintiliani , M. ; Kahnt , A. ; Wöfle , T. ; Hieringer , W. ; Vázquez , P. ; Göling , A. ; Guldi , D. M. ; Torres , T. Synthesis and photoinduced electron-transfer properties of phthalocyanine–[60]fullerene conjugates . Chem. Eur. J. 2008 , 14 , 3765 – 3775 .
  • Baffreau , J. ; Ordronneau , L. ; Leroy-Lhez , S. ; Hudhomme , P. Synthesis of perylene-3,4-mono(dicarboximide)−fullerene C60 dyads as new light-harvesting systems . J. Org. Chem. 2008 , 73 , 6142 – 6147 .
  • Prato , M. ; Maggini , M. Fulleropyrrolidines: A family of full-fledged fullerene derivatives . Acc. Chem. Res. 1998 , 31 , 519 – 526 .
  • Zhang , X. ; Gan , L. B. ; Huang , S. H. ; Shi , Y. R. Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C60 and amino acid esters . J. Org. Chem. 2004 , 69 , 5800 – 5802 .
  • Wang , G. W. ; Chen , X. P. ; Cheng , X. Unexpected reactions of [60]fullerene involving tertiary amines and insight into the reaction mechanisms . Chem. Eur. J. 2006 , 12 , 7246 – 7253 .
  • Maggini , M. ; Scorrano , G. ; Prato , M. Addition of azomethine ylides to C60: Synthesis, characterization, and functionalization of fullerene pyrrolidines. J. Am. Chem. Soc. 1993, 115, 9798–9799.
  • Maggini , M. ; Karlsson , A. ; Pasimeri , L. ; Scorrano , G. ; Prato , M. ; Valli , L. Synthesis of N-acylated fulleropyrrolidines: New materials for the preparation of Langmuir-Blodgett films containing fullerenes . Tetrahedron Lett. 1994 , 35 , 2985 – 2988 .
  • de la Cruz , P. ; de la Hoz , A. ; Font , L. M. ; Langa , F. ; Pérez-Rodríguez , M. C. Solvent-free phase transfer catalysis under microwaves in fullerene chemistry. A convenient preparation of N-alkylpyrrolidino[60]fullerenes . Tetrahedron Lett. 1998 , 39 , 6053 – 6056 .
  • Deviprasad , G. R. ; Rahman , M. S. ; D'Souza , F. N-(2,4-Dinitrophenyl)-2-phenylfulleropyrrolidine: An electroactive organofullerene dyad . Chem. Commun. 1999 , 849 – 850 .
  • Erdélyi , M. ; Gogoll , A. Rapid microwave promoted sonogashira coupling reactions on solid phase . J. Org. Chem. 2003 , 68 , 6431 – 6434 .
  • Zhang , J. M. ; Yang , W. ; He , P. ; Zhu , S. Z. ; Wang , S. Microwave-promoted one-pot three-component reaction to [60]fulleropyrrolidine derivatives . Synth. Commun. 2005 , 35 , 89 – 96 .
  • Seipel , K. R. ; Platt , Z. H. ; Nguyen , M. ; Holland , A. W. Microwave-assisted synthesis of phenylene-bridged aminophosphine ligands: Acceleration of N-arylation and aryl fluoride phosphorylation reactions . J. Org. Chem. 2008 , 73 , 4291 – 4294 .
  • de la Cruz , P. ; de la Hoz , A. ; Langa , F. ; Martín , N. ; Pérez , M. C. ; Sánchez , L. N-Arylation of pyrrolidino[39,49:1,2][60]fullerene: Synthesis under solvent-free conditions and electrochemistry of new C60–acceptor dyads . Eur. J. Org. Chem. 1999 , 3433 – 3436 .
  • Langa , F. ; de la Cruz , P. ; Espíldora , E. ; García , J. J. ; Pérez , M. C. ; de la Hoz , A. Fullerene chemistry under microwave irradiation . Carbon 2000 , 38 , 1641 – 1646 .
  • Kräetschmer , W. ; Lamb , L. D. ; Fostiropoulos , K. ; Huffman , D. R. Solid C60: A new form of carbon . Nature 1990 , 347 , 354 – 358 .

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