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Volumn 158, Issue 3-4, 2010, Pages 279-285

Experimental and theoretical investigation of reaction of aniline with dimethyl carbonate catalyzed by acid-base bifunctional ionic liquids

Author keywords

Acid base cooperativity; Ionic liquid; Mechanism; Simulation

Indexed keywords

ACID BASE; BASIC IONIC LIQUID; BASIC SITES; BIFUNCTIONAL; CATALYZED REACTIONS; CHARGE PROPERTIES; COOPERATIVITY; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIMETHYL CARBONATE; EFFICIENT CATALYSTS; ELECTROPHILICITY; HIGH REACTIVITY; IMIDAZOLIUM; NUCLEOPHILICITIES; SIMULATION; THEORETICAL INVESTIGATIONS;

EID: 78649722732     PISSN: 09205861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cattod.2010.03.060     Document Type: Conference Paper
Times cited : (33)

References (29)
  • 2
    • 0001491415 scopus 로고
    • Synthesis and herbicidal activity of α-heterocyclic carbinol carbamates
    • T.T. Wu, J.M. Huang, D.A. Noel, and G.D. Dill Synthesis and herbicidal activity of α-heterocyclic carbinol carbamates J. Agric. Food Chem. 35 1987 817 823
    • (1987) J. Agric. Food Chem. , vol.35 , pp. 817-823
    • Wu, T.T.1    Huang, J.M.2    Noel, D.A.3    Dill, G.D.4
  • 3
    • 0033515870 scopus 로고    scopus 로고
    • Neutral acylation (protection) of the indole nitrogen: A simple synthesis of indole-1-carboxylates, indole-1-thiocarboxylates and indole-1-carboxamides
    • J.E. Macor, A. Cuff, and L. Cornelius Neutral acylation (protection) of the indole nitrogen: a simple synthesis of indole-1-carboxylates, indole-1-thiocarboxylates and indole-1-carboxamides Tetrahedron Lett. 40 1999 2733 2736
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2733-2736
    • MacOr, J.E.1    Cuff, A.2    Cornelius, L.3
  • 4
    • 33751391068 scopus 로고
    • An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates
    • J.S. Norwick, N.A. Powell, T.M. Nguyen, and G. Noronha An improved method for the synthesis of enantiomerically pure amino acid ester isocyanates J. Org. Chem. 57 1992 7364 7366
    • (1992) J. Org. Chem. , vol.57 , pp. 7364-7366
    • Norwick, J.S.1    Powell, N.A.2    Nguyen, T.M.3    Noronha, G.4
  • 5
    • 0032572851 scopus 로고    scopus 로고
    • An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas
    • R. Batey, V. Santhakumar, C. Yoshina-Ishii, and S. Taylor An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas Tetrahedron Lett. 39 1998 6267 6270
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6267-6270
    • Batey, R.1    Santhakumar, V.2    Yoshina-Ishii, C.3    Taylor, S.4
  • 6
    • 0036558347 scopus 로고    scopus 로고
    • Catalytic activity of mesoporous silica for synthesis of methyl N-phenyl carbamate from dimethyl carbonate and aniline
    • K. Naonobu, F. Haruhisa, and N. Yukinori Catalytic activity of mesoporous silica for synthesis of methyl N-phenyl carbamate from dimethyl carbonate and aniline Catal. Lett. 80 2002 47 51
    • (2002) Catal. Lett. , vol.80 , pp. 47-51
    • Naonobu, K.1    Haruhisa, F.2    Yukinori, N.3
  • 8
    • 0037043070 scopus 로고    scopus 로고
    • Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis
    • M. Curini, F. Epifano, F. Maltese, and O. Rosati Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis Tetrahedron Lett. 43 2002 4895 4897
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4895-4897
    • Curini, M.1    Epifano, F.2    Maltese, F.3    Rosati, O.4
  • 9
    • 54049097048 scopus 로고    scopus 로고
    • Non-phosgene route for the synthesis of methyl phenyl carbamate using ordered AlSBA-15 catalyst
    • N. Lucasa, A.P. Amrutea, and K. Palraja Non-phosgene route for the synthesis of methyl phenyl carbamate using ordered AlSBA-15 catalyst J. Mol. Catal. A 295 2008 29 33
    • (2008) J. Mol. Catal. A , vol.295 , pp. 29-33
    • Lucasa, N.1    Amrutea, A.P.2    Palraja, K.3
  • 10
    • 15444372044 scopus 로고    scopus 로고
    • Dimethyl carbonate as an ambident electrophile
    • P. Tundo, L. Rossi, and A. Loris Dimethyl carbonate as an ambident electrophile J. Org. Chem. 70 2005 2219 2224
    • (2005) J. Org. Chem. , vol.70 , pp. 2219-2224
    • Tundo, P.1    Rossi, L.2    Loris, A.3
  • 11
    • 0742320252 scopus 로고    scopus 로고
    • Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions
    • M. Distasoa, and E. Quaranta Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions Tetrahedron 60 2004 1531 1539
    • (2004) Tetrahedron , vol.60 , pp. 1531-1539
    • Distasoa, M.1    Quaranta, E.2
  • 12
    • 0028466805 scopus 로고
    • Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts
    • Z.H. Fu, and O. Yoshio Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts J. Mol. Catal. 91 1994 399 405
    • (1994) J. Mol. Catal. , vol.91 , pp. 399-405
    • Fu, Z.H.1    Yoshio, O.2
  • 14
    • 0000115570 scopus 로고
    • A convenient method for the conversion of amines to carbamates
    • S. Raucher, and S.D. Jones A convenient method for the conversion of amines to carbamates Synth. Commun. 15 1985 1025 1031
    • (1985) Synth. Commun. , vol.15 , pp. 1025-1031
    • Raucher, S.1    Jones, S.D.2
  • 15
    • 0000894880 scopus 로고
    • A general strategy for elaboration of the dithiocarbonyl functionality, -(C:O)SS-: Application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acids
    • G. Barany, A.L. Schroll, A.W. Mott, and D.A. Halsrud A general strategy for elaboration of the dithiocarbonyl functionality, -(C:O)SS-: application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acids J. Org. Chem. 48 1983 4750 4761
    • (1983) J. Org. Chem. , vol.48 , pp. 4750-4761
    • Barany, G.1    Schroll, A.L.2    Mott, A.W.3    Halsrud, D.A.4
  • 17
    • 27644550552 scopus 로고    scopus 로고
    • Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate
    • P. Tundo, S. Bressanello, A. Loris, and G. Sathicq Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate Pure Appl. Chem. 77 2005 1719 1725
    • (2005) Pure Appl. Chem. , vol.77 , pp. 1719-1725
    • Tundo, P.1    Bressanello, S.2    Loris, A.3    Sathicq, G.4
  • 19
    • 0037020638 scopus 로고    scopus 로고
    • The syntheses of carbamates from reactions of primary and secondary aliphatic amines with dimethyl carbonate in ionic liquids
    • T. Sima, S. Guo, F. Shi, and Y.Q. Deng The syntheses of carbamates from reactions of primary and secondary aliphatic amines with dimethyl carbonate in ionic liquids Tetrahedron Lett. 43 2002 8145 8147
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8145-8147
    • Sima, T.1    Guo, S.2    Shi, F.3    Deng, Y.Q.4
  • 20
    • 34248231984 scopus 로고    scopus 로고
    • Synthesis of carbamates from aliphatic amines and dimethyl carbonate catalyzed by acid functional ionic liquids
    • H.C. Zhou, F. Shi, X. Tian, Q.H. Zhang, and Y.Q. Deng Synthesis of carbamates from aliphatic amines and dimethyl carbonate catalyzed by acid functional ionic liquids J. Mol. Catal. A: Chem. 271 2007 89 92
    • (2007) J. Mol. Catal. A: Chem. , vol.271 , pp. 89-92
    • Zhou, H.C.1    Shi, F.2    Tian, X.3    Zhang, Q.H.4    Deng, Y.Q.5
  • 21
    • 58149336789 scopus 로고    scopus 로고
    • N-heterocyclic carbomethoxylation catalyzed by ionic liquids in the presence of dimethyl carbonate
    • X.L. Fu, Z. Zhang, C.M. Li, L.B. Wang, H.Y. Ji, Y. Yang, T. Zou, and G.H. Gao N-heterocyclic carbomethoxylation catalyzed by ionic liquids in the presence of dimethyl carbonate Catal. Commun. 10 2009 665 668
    • (2009) Catal. Commun. , vol.10 , pp. 665-668
    • Fu, X.L.1    Zhang, Z.2    Li, C.M.3    Wang, L.B.4    Ji, H.Y.5    Yang, Y.6    Zou, T.7    Gao, G.H.8
  • 22
    • 35748980308 scopus 로고    scopus 로고
    • General performance of density functionals
    • S.F. Sousa, P.A. Fernandes, and M.J. Ramos General performance of density functionals J. Phys. Chem. A 111 2007 10439 10452
    • (2007) J. Phys. Chem. A , vol.111 , pp. 10439-10452
    • Sousa, S.F.1    Fernandes, P.A.2    Ramos, M.J.3
  • 24
    • 33845282175 scopus 로고
    • Selective mono-N-alkylation of aromatic amines by dialkyl carbonate under gas-liquid phase-transfer catalysis (GL-PTC) conditions
    • F. Trotta, P. Tundo, and G. Moraglio Selective mono-N-alkylation of aromatic amines by dialkyl carbonate under gas-liquid phase-transfer catalysis (GL-PTC) conditions J. Org. Chem. 52 1987 1300 1304
    • (1987) J. Org. Chem. , vol.52 , pp. 1300-1304
    • Trotta, F.1    Tundo, P.2    Moraglio, G.3
  • 26
    • 33845554742 scopus 로고
    • Dialkylimidazolium chloroaluminate melts: A new class of room-temperature ionic liquids for electrochemistry, spectroscopy, and synthesis
    • J.S. Wilkes, J.A. Levisky, R.A. Wilson, and C.L. Hussey Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy, and synthesis Inorg. Chem. 21 1982 1263 1264
    • (1982) Inorg. Chem. , vol.21 , pp. 1263-1264
    • Wilkes, J.S.1    Levisky, J.A.2    Wilson, R.A.3    Hussey, C.L.4
  • 27
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids. Solvents for synthesis and catalysis
    • T. Welton Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem. Rev. 99 1999 2071 2083
    • (1999) Chem. Rev. , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 28
    • 29444456436 scopus 로고    scopus 로고
    • DFT study of the monomers and dimers of 2-pyrrolidone: Equilibrium structures, vibrational, orbital, topological, and NBO analysis of hydrogen-bonded interactions
    • A.E. Shchavlev, A.N. Pankratov, V.B. Borodulin, and O.A. Chaplygina DFT study of the monomers and dimers of 2-pyrrolidone: equilibrium structures, vibrational, orbital, topological, and NBO analysis of hydrogen-bonded interactions J. Phys. Chem. A 109 2005 10982 10996
    • (2005) J. Phys. Chem. A , vol.109 , pp. 10982-10996
    • Shchavlev, A.E.1    Pankratov, A.N.2    Borodulin, V.B.3    Chaplygina, O.A.4
  • 29
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • A.E. Reed, L.A. Curtiss, and F. Weinhold Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 88 1988 899 926
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3


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