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Volumn 44, Issue 8, 2003, Pages 1679-1683

Hydroaminomethylation of olefins using a rhodium carbene catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; ALKENE DERIVATIVE; AMINE; AROMATIC COMPOUND; CARBENE; RHODIUM COMPLEX; SOLVENT;

EID: 0037450462     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00008-X     Document Type: Article
Times cited : (58)

References (26)
  • 1
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    • Reviews
    • Reviews: Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199-207; (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
    • (1998) Chem. Rev. , vol.98 , pp. 675-703
    • Müller, T.E.1    Beller, M.2
  • 2
    • 0033461968 scopus 로고    scopus 로고
    • Reviews: Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703; (b) Yamamoto, Y.; Radhakrishnan, U. Chem. Soc. Rev. 1999, 28, 199-207; (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 199-207
    • Yamamoto, Y.1    Radhakrishnan, U.2
  • 8
    • 35448936556 scopus 로고    scopus 로고
    • Reviews
    • Reviews: (a) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222; (b) Herrmann W. A., Angew. Chem., Int. Ed. 2002, 41, 1290-1309; (c) Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50-64.
    • (2001) Adv. Organomet. Chem. , vol.46 , pp. 181-222
    • Jafarpour, L.1    Nolan, S.P.2
  • 9
    • 0037090932 scopus 로고    scopus 로고
    • Reviews: (a) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222; (b) Herrmann W. A., Angew. Chem., Int. Ed. 2002, 41, 1290-1309; (c) Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50-64.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1290-1309
    • Herrmann, W.A.1
  • 10
    • 0036541546 scopus 로고    scopus 로고
    • Reviews: (a) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222; (b) Herrmann W. A., Angew. Chem., Int. Ed. 2002, 41, 1290-1309; (c) Hillier, A. C.; Nolan, S. P. Platinum Met. Rev. 2002, 46, 50-64.
    • (2002) Platinum Met. Rev. , vol.46 , pp. 50-64
    • Hillier, A.C.1    Nolan, S.P.2
  • 16
    • 0012981222 scopus 로고    scopus 로고
    • note
    • 2Rh (550.98): C, 63.22; H, 6.58; N, 5.08; Found: C, 63.08; H, 6.34; N, 5.05.
  • 17
    • 0012989597 scopus 로고    scopus 로고
    • 2=1:5) and the reaction was carried out for 12 h at a temperature of 95°C (total pressure at 95°C was ca. 66 bar). After the reaction, the autoclave was cooled slowly to 0-5°C and slowly depressurized. The reaction mixture was analyzed by gas chromatography with bis(methoxyethyl)ether as an internal standard. N-Hexylpiperidine and (2-methyl-1-pentyl)piperidine were identified by comparison with authentic samples by GC (HP5890 series; column: HP5 (Crosslinked 5% PH ME Siloxane) 30 m, 0.25 mm, 0.25 μm). The products were also confirmed by GC MS and NMR
    • 2=1:5) and the reaction was carried out for 12 h at a temperature of 95°C (total pressure at 95°C was ca. 66 bar). After the reaction, the autoclave was cooled slowly to 0-5°C and slowly depressurized. The reaction mixture was analyzed by gas chromatography with bis(methoxyethyl)ether as an internal standard. N-Hexylpiperidine and (2-methyl-1-pentyl)piperidine were identified by comparison with authentic samples by GC (HP5890 series; column: HP5 (Crosslinked 5% PH ME Siloxane) 30 m, 0.25 mm, 0.25 μm). The products were also confirmed by GC MS and NMR.
  • 19
    • 0013036531 scopus 로고    scopus 로고
    • 2 was predominant in toluene as the solvent and increased with temperature. The Rh-carbene complex was found to be stable (no formation of metal particles) up to a temperature of 140°C
    • 2 was predominant in toluene as the solvent and increased with temperature. The Rh-carbene complex was found to be stable (no formation of metal particles) up to a temperature of 140°C.


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