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Volumn 121, Issue 1, 1999, Pages 63-70

Electronically dissymmetric DIPHOS derivatives give higher n:i regioselectivity in rhodium-catalyzed hydroformylation than either of their symmetric counterparts

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM COMPLEX; LIGAND; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX;

EID: 0033550486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982117h     Document Type: Article
Times cited : (120)

References (56)
  • 2
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    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford
    • (b) Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp 101-223.
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 101-223
    • Tkatchenko, I.1
  • 14
    • 0345263073 scopus 로고    scopus 로고
    • (to Union Carbide) U.S. Patent 4,748,261 1988; 4,769,498, 1988
    • (a) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. (to Union Carbide) U.S. Patent 4,748,261 1988; 4,769,498, 1988.
    • Billig, E.1    Abatjoglou, A.G.2    Bryant, D.R.3
  • 25
    • 0344831696 scopus 로고    scopus 로고
    • note
    • 7c In a series of bidentate chelating phosphines containing xanthene-like ligand backbones, the bite angle was varied from 102° to 131°, with minimal change in the steric or electronic properties of the ligand. The resulting n:i ratio increased from 6.7 to 80.5 in the hydroformylation of 1-octene at 80 °C.
  • 26
    • 0345694717 scopus 로고    scopus 로고
    • note
    • 12 which is the ratio seen early in the reaction. For consistency, we are now reporting ratios obtained after 120-250 turnovers (20-50% conversion) for all ligands.
  • 31
    • 0345263071 scopus 로고    scopus 로고
    • note
    • 12
  • 34
    • 0000300885 scopus 로고    scopus 로고
    • 20c for phosphine interchange. The transition state for Berry pseudorotation is a square-based pyramid that we believe would be more stable than the transition state for a Meakin mechansm which resembles an edge-protonated tetrahedron. (a) Buisman, G. J. H.; van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1997, 16, 5681-5687. (b) Castellanos-Páez, A.; Castillón, S.; Claver, C.; van Leeuwen, P. W. N. M.; de Lange, W. G. J. Organometallics 1998, 17, 2543-2552. (c) Meakin, P.; Muetterties, E. L.; Jesson, J. P. J. Am. Chem. Soc. 1972, 94, 5271.
    • (1997) Organometallics , vol.16 , pp. 5681-5687
    • Buisman, G.J.H.1    Van Der Veen, L.A.2    Kamer, P.C.J.3    Van Leeuwen, P.W.N.M.4
  • 35
    • 0000300885 scopus 로고    scopus 로고
    • 20c for phosphine interchange. The transition state for Berry pseudorotation is a square-based pyramid that we believe would be more stable than the transition state for a Meakin mechansm which resembles an edge-protonated tetrahedron. (a) Buisman, G. J. H.; van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1997, 16, 5681-5687. (b) Castellanos-Páez, A.; Castillón, S.; Claver, C.; van Leeuwen, P. W. N. M.; de Lange, W. G. J. Organometallics 1998, 17, 2543-2552. (c) Meakin, P.; Muetterties, E. L.; Jesson, J. P. J. Am. Chem. Soc. 1972, 94, 5271.
    • (1998) Organometallics , vol.17 , pp. 2543-2552
    • Castellanos-Páez, A.1    Castillón, S.2    Claver, C.3    Van Leeuwen, P.W.N.M.4    De Lange, W.G.J.5
  • 36
    • 0000714740 scopus 로고
    • 20c for phosphine interchange. The transition state for Berry pseudorotation is a square-based pyramid that we believe would be more stable than the transition state for a Meakin mechansm which resembles an edge-protonated tetrahedron. (a) Buisman, G. J. H.; van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1997, 16, 5681-5687. (b) Castellanos-Páez, A.; Castillón, S.; Claver, C.; van Leeuwen, P. W. N. M.; de Lange, W. G. J. Organometallics 1998, 17, 2543-2552. (c) Meakin, P.; Muetterties, E. L.; Jesson, J. P. J. Am. Chem. Soc. 1972, 94, 5271.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5271
    • Meakin, P.1    Muetterties, E.L.2    Jesson, J.P.3
  • 38
    • 0345263070 scopus 로고    scopus 로고
    • note
    • A ≤ 1 is picked.
  • 39
    • 0345263069 scopus 로고    scopus 로고
    • note
    • A = 0.844, obtained in the previous calculation, was selected.
  • 40
    • 0344400221 scopus 로고    scopus 로고
    • note
    • A = 1.144.
  • 41
    • 0345694714 scopus 로고    scopus 로고
    • note
    • A = 0.877.
  • 42
    • 0344400220 scopus 로고    scopus 로고
    • note
    • A = 1.095.
  • 43
    • 0344400219 scopus 로고    scopus 로고
    • note
    • 3 (7) complex. See the Supporting Information.
  • 44
    • 0345263067 scopus 로고    scopus 로고
    • note
    • 3,H)]Rh(CO)(alkene)H which has the electron-withdrawing aryl groups on the equatorial phosphine was calculated to be 4.9 and the n:i ratio for the minor isomer with the electron-withdrawing aryl groups on the apical phosphine was calculated to be 0.7.
  • 54
    • 0345694709 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for synthesis and characterization.
  • 55
    • 0344400215 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for characterization.
  • 56
    • 0344400214 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for X-ray data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.