Nitration of Simple Aromatics with NO₂ under Air Atmosphere in the Presence of Novel Brønsted Acidic Ionic Liquids

References

• Suzuki , H. , Tatsumi , A. , Suzuki , H. M. and Maeda , K. 1995 . A novel non‐acidic method for the preparation of 2,2,2‐trifluoro‐1‐(3‐nitrophenyl)ethanone and 1‐nitro‐3‐trifluoromethylbenzene, versatile starting materials for trifluoromethyl‐containing aromatic compounds . Synthesis , : 1353 – 1354 . See, for example. (a)
   Web of Science ®Google Scholar
• Suzuki , H. and Mori , T. 1994 . Ozone‐mediated nitration of chloro‐ and bromo‐benzenes and some methyl derivatives with nitrogen dioxide: high ortho‐directing trends of the chlorine and bromine substituents . J. Chem. Soc., Perkin Trans. , 2 : 479 – 484 .
   Google Scholar
• Suzuki , H. , Mori , T. and Maeda , K. 1994 . Ozone‐mediated reaction of polychlorobenzenes and some related halogeno compounds with nitrogen dioxides: a novel non‐acid methodology for the selective mononitration of moderately deactivated aromatic systems . Synthesis , : 841 – 845 .
   Web of Science ®Google Scholar
• Suzuki , H. , Tomaru , J. and Murashima , T. 1996 . Iron(III)‐catalysed nitration of non‐activated and moderately activated arenas with nitrogen dioxide‐molecular oxygen under neutral conditions . J. Chem. Soc., Perkin Trans. , 1 : 2385 – 2389 .
   Google Scholar
• Barrett , A. G. M. , Braddock , D. C. , Ducray , R. , Mckinnell , R. M. and Waller , F. J. 2000 . Lanthanide triflate and triflide catalyzed atom economic nitration of fluoro arenes . Synlett , : 57 – 59 .
   Web of Science ®Google Scholar
• Waller , F. J. , Barrett , A. G. M. , Braddock , D. C. and Ramprasad , D. 1997 . Lanthanide(III) triflates as recyclable catalysts for atom economic aromatic nitration . Chem. Commun. , : 613 – 615 .
   Web of Science ®Google Scholar
• Delaude , L. , Laszlo , P. and Smith , K. 1993 . Heightened selectivity in aromatic nitrations and chlorinations by the use of sokid supports and catalysts . Acc. Chem. Res. , 26 : 607 – 613 .
   Web of Science ®Google Scholar
• Gigante , B. , Prazeres , A. O. and Marcelo‐Curto , M. J. 1995 . Mild and selective nitration by claycop . J. Org. Chem. , 60 : 3445 – 3447 .
   Web of Science ®Google Scholar
• Kwok , T. J. , Jayasuriya , K. , Damavarapu , R. and Brodman , B. W. 1994 . Application of H‐ZSM‐5 zeolite for regioselective mononitration of toluene . J. Org. Chem. , 59 : 4939 – 4942 .
   Web of Science ®Google Scholar
• Vessena , D. , Kogelbauer , A. and Prins , R. 2000 . Potential routes for the nitration of toluene and nitrotoluene with solid acids . Catal Today , 60 : 275 – 287 .
   Web of Science ®Google Scholar
• Dagade , S. P. , Waghmode , S. B. , Kadam , V. S. and Dongare , M. K. 2002 . Vapor phase nitration of toluene using dilute nitric acid and molecular modeling studies over beta zeolite . Appl. Catal., A , 226 : 49 – 61 .
   Web of Science ®Google Scholar
• Peng , X. , Suzuki , H. and Lu , C. 2001 . Zeolite‐assisted nitration of neat toluene and chlorobenzene with a nitrogen dioxide/molecular oxygen system: remarkable enhancement of para‐selectivity . Tetrahedron Lett. , 42 : 4357 – 4359 .
   Web of Science ®Google Scholar
• Sheldon , R. 2001 . Catalytic reactions in ionic liquids . Chem. Commun. , : 2399 – 2407 . See, for example, (a)
   PubMed Web of Science ®Google Scholar
• Dupont , J. , Souza , R. F. and Suarez , P. A. Z. 2002 . Ionic liquid (molten salt) phase organometallic catalysis . Chem. Rev. , 102 : 3667 – 3692 .
   PubMed Web of Science ®Google Scholar
• Cole , A. C. , Jensen , J. L. , Ntai , I. , Tran , K. L. T. and Weaver , K. J. 2002 . Novel Brøsted acidic ionic liquids and their use as dual solvent‐catalysts . J. Am. Chem. Soc. , 124 : 5962 – 5963 .
   PubMed Web of Science ®Google Scholar
• Gui , J. Z. , Ban , J. Y. , Cong , X. H. , Zhang , X. T. and Sun , Z. L. 2005 . Selective alkylation of phenol with tert‐butyl alcohol catalyzed by Brøsted acidic imidazolium salts . J. Mol. Catal. A , 225 : 27 – 31 .
   Web of Science ®Google Scholar
• Joseph , T. , Sahoo , S. and Halligudi , S. B. 2005 . Brøsted acidic ionic liquids: a green, efficient and reusable catalyst system and reaction medium for Fischer esterification . J. Mol Catal. A , 234 : 107 – 110 .
   Web of Science ®Google Scholar
• Angueira , E. J. and White , M. G. 2005 . Arene carbonylation in acidic, chloro aluminate ionic liquids . J. Mol. Catal. A , 227 : 51 – 58 .
   Web of Science ®Google Scholar
• Li , D. M. , Shi , F. , Peng , J. J. , Guo , S. and Deng , Y. Q. 2004 . Application of functional ionic liquids possessing two adjacent acid sites for acetalization of aldehydes . J. Org. Chem. , 69 : 3582 – 3585 .
   PubMed Web of Science ®Google Scholar
• Swatloski , R. , Holbrey , J. , Memon , S. , Caldwell , G. , Caldwell , K. and Rogers , R. 2004 . Using Caenorhabditis elegans to probe toxicity of 1‐alkyl‐3‐methylimidazolium chloride based ionic liquids . Chem. Commun. , : 668 – 669 .
   PubMed Web of Science ®Google Scholar
• Du , Z. Y. , Li , Z. P. , Guo , S. , Zhong , J. , Zhu , L. Y. and Deng , Y. Q. 2005 . Investigation of physicochemical properties of lactam‐based Brøsted acidic ionic liquids . J. Phys. Chem. B , 109 : 19542 – 19546 .
   PubMed Web of Science ®Google Scholar
• Qiao , K. and Yokoyama , C. 2004 . Nitration of aromatic compounds with nitric acid catalyzed by ionic liquids . Chem. Lett. , 33 : 808 – 809 .
   Web of Science ®Google Scholar
• Smith , K. , Liu , S. F. and El‐Hiti , G. A. 2005 . Regioselective mononitration of simple aromatic compounds under mild conditions in ionic liquids . Ind. Eng. Chem. Res. , 44 : 8611 – 8615 .
   Web of Science ®Google Scholar
• Yang , Y. L. and Kou , Y. 2004 . Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe . Chem. Commun. , : 226 – 227 .
   PubMed Web of Science ®Google Scholar
• Parry , E. P. 1963 . An infrared of pyridine adsorbed on acidic solids, characterization of surface acidity . J. Catal. , 2 : 371 – 379 .
   Web of Science ®Google Scholar
• Schofield , K. 1980 . Aromatic Nitration 77 Cambridge University Press .
   Google Scholar