Green Synthesis: Aromatic Nitrations in Room-Temperature Ionic Liquids

ACS Symposium Series

Volumn 818, Issue , 2002, Pages 134-146

  Handy, Scott T ^a   Egrie, Cristina R ^a  

^a BINGHAMTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347646761     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2002-0818.ch011     Document Type: Article

References (17)

1. Taylor, R. "Electrophilic Aromatic Substitution." John Wiley and Sons: New York, 1990.
2. Horning, E.C., ed. "p- Chloroacetylacetanilide." Org. Synth. Coll. Vol. III, John Wiley and Sons, Inc.: New York, 1955, 183-184.
3. Blatt, A.H., ed. "o-Nitroaniline." Org. Synth. Coll. Vol. I, John Wiley and Sons, Inc.: New York, 1941, 388-289.
4. For an example of nitrations using acidic zeolites, see: Smith, K.E.; Musson, A.; DeBoos. G.A. "Superior methodology for the nitration of simple aromatic compounds." Chem. Commun. 1996, 469-470.
5. For an example of nitrations using exchanged clays, see: Cornelis, A.; Gerstmans, A.; Laszlo, P. "Regioselective Liquid-phase Toluene Nitration with Modified Clays as Catalysts." Chem. Lett. 1988, 1839-1842.
6. For an example of nitrations using acidic ion-exchange resins, see: Olah, G.A.; Malhotra, R.; Narang, S.C. "Aromatic Substitution. 43. Perfluorinated Resinsulfonic Acid Catalyzed Nitration of Aromatics." J. Org. Chem. 1978, 48, 4628-4630.
7. For an example of nitrations using acidic ion-exchange resins, see: Olah, G.A.; Malhotra, R.; Narang, S.C. "Aromatic Substitution. 43. Perfluorinated Resinsulfonic Acid Catalyzed Nitration of Aromatics." J. Org. Chem. 1978, 48, 4628-4630.
8. Waller, F.J.; Barrett. A.G.M.; Braddock, D.C.; Ramprasad, D. "Lanthanide (III) Triflates as Recyclable Catalysts for Atom Economic Aromatic Nitration." Chem. Commun. 1997, 613-614.
9. For a review of room temperature ionic liquids, see: Welton, T.; "Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis." Chem. Rev. 2000, 100, 2071-2083
10. For a review of the use of transition-metal catalysts in room temperature ionic liquids, see: Wasserscheid, P.; Keim, W. "Ionic Liquids - New "Solutions for Transition Metal Catalysis." Angew. Chem. Int. Ed. 2000, 39, 3772-3789
11. Laali, K.K.; Gettwert, V.J. "Electrophilic Nitration of Aromatics in Ionic Liquids Solvents." J. Org. Chem. 2001, 66, 35-40.
12. MacFarlane, D.R.; Meakin, P.; Sun, J.; Amini, N.; Forsyth, M. "Pyrrolidinium Imides: A New Family of Molten Salts and Conductive Plastic Crystal Phases." J. Phys. Chem. B 1999, 103, 4164-4170
13. For a recent study of the differences between various acyl nitrates generated in situ, see: Smith, K.; Gibbins, T.; Millar, R.W.; Claridge, R.P. "A Novel Method for the Nitration of Deactivated Aromatic Compounds." J. Chem. Soc., Perkins Trans. I 2000, 2753-2758.
14. For a review, see: Kobayashi, S. "Rare-Earth-Metal Trifluoromethanesulfonates as Water-Tolerant Lewis-Acid Catalysts in Organic-Synthesis." Synlett 1994, 689-701.
15. Manabe, K.; Kobayashi, S. "Effects of Metal Cations in Lewis Acid-Surfactant Combined Catalyst-Mediated Aldol Reactions in Water." Synlett 1999, 547-548. And references cited therein.
16. For examples of this, see: Laszlo, P.; Vandormael, J. "Regioselective Nitration of Aromatic Hydrocarbons by Metallic Nitrates on the K10 Montmorillonite under Menke Conditions." Chem. Lett. 1988, 1843-1846. Cornelis, A.; Laszlo, P.; Pennetreau, P. "Nitration of Estrone into 2-Nitroestrone by Clay-supported Ferric Nitrate." J. Org. Chem. 1983, 48, 4771-4472. And references cited therein.
17. For examples of this, see: Laszlo, P.; Vandormael, J. "Regioselective Nitration of Aromatic Hydrocarbons by Metallic Nitrates on the K10 Montmorillonite under Menke Conditions." Chem. Lett. 1988, 1843- 1846. Cornelis, A.; Laszlo, P.; Pennetreau, P. "Nitration of Estrone into 2-Nitroestrone by Clay-supported Ferric Nitrate." J. Org. Chem. 1983, 48, 4771-4472. And references cited therein.