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Volumn 45, Issue 21, 2006, Pages 8785-8798

Synthesis and coordination behavior of planar-chiral ferrocene alkenylphosphines

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EID: 33750343775     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic061278g     Document Type: Article
Times cited : (44)

References (95)
  • 3
  • 11
    • 0006834540 scopus 로고
    • Examples of FcCH=CHR alkenes (R = Me or Ph) substituted in position 2 of the ferrocene unit are even less common. See, e.g.: (b) Toma, Š.; Kaluzayova, E. Chem. Zvesti 1969, 23, 540-552.
    • (1969) Chem. Zvesti , vol.23 , pp. 540-552
    • Toma, Š.1    Kaluzayova, E.2
  • 17
    • 0001120785 scopus 로고    scopus 로고
    • This diphosphine was also obtained a side product from the attempted synthesis of a chiral, azacrown-substituted ferrocenyldiphosphine: (b) Landis, C. R.; Sawyer, R. A.; Somsook, E. Organometallics 2000, 19, 994-1002.
    • (2000) Organometallics , vol.19 , pp. 994-1002
    • Landis, C.R.1    Sawyer, R.A.2    Somsook, E.3
  • 18
    • 0035808985 scopus 로고    scopus 로고
    • A related 1,1′-bis(alkenyl)-2,2′-diphosphine as a precursor for chiral ferrocene diphosphine can be found in: (c) Kang, J.; Lee, J. H.; Choi, J. S. Tetrahedron: Asymmetry 2001, 12, 33-35.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 33-35
    • Kang, J.1    Lee, J.H.2    Choi, J.S.3
  • 45
    • 33750342865 scopus 로고    scopus 로고
    • note
    • p)-chiral, the descriptor specifying chirality at the 1,2-disubstituted cyclopentadienyl plane is omitted for clarity.
  • 46
    • 0001224666 scopus 로고    scopus 로고
    • p)-1-[2-(diphenylphosphino)ferrocenyl]ethyl acetate as a chiral auxiliary. For reference, see: Kuehne, M. E.; Bandarage, U. K. J. Org. Chem. 1996, 61, 1175-1179.
    • (1996) J. Org. Chem. , vol.61 , pp. 1175-1179
    • Kuehne, M.E.1    Bandarage, U.K.2
  • 49
    • 84979404437 scopus 로고
    • and references therein
    • Wittig, G.; Schöllkopf, U. Chem. Ber. 1954, 87, 1318-1330 and references therein.
    • (1954) Chem. Ber. , vol.87 , pp. 1318-1330
    • Wittig, G.1    Schöllkopf, U.2
  • 58
    • 33750294599 scopus 로고    scopus 로고
    • note
    • 3OD) stand against it.
  • 59
    • 1842692143 scopus 로고
    • 2 = 216°. N.B. The ring puckering parameters should be considered informative only because of the different bond lengths within the metallacycle.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1354-1358
    • Cremer, D.1    Pople, J.A.2
  • 60
    • 33750285329 scopus 로고    scopus 로고
    • note
    • 2) moieties in the Cambridge Structural Database (CSD; 35 structures) revealed that there is no pronounced correlation between the coordination distance (Pd-Cg) and the C=C bond length. This is probably because an influence of the double bond substituent (R) on the double bond length is comparable with that of coordination. Nevertheless, the bond lengths observed for 8 are in accordance with mean values from CSD. Source: Cambridge Structural Database version 5.27 of Nov 2005 with updates of Jan 2006.
  • 61
    • 33750325975 scopus 로고    scopus 로고
    • note
    • 27b and 2 in diethyl ether/heptane. However, NMR analysis showed that no reaction took place at room temperature after 24 h.
  • 64
    • 33750288233 scopus 로고    scopus 로고
    • note
    • 4(cod)] at elevated temperature were always accompanied by a partial decomposition resulting into a formation of dark insoluble materials. Decomposing carbonyl complexes are the most likely source of free CO.
  • 65
    • 33750381141 scopus 로고    scopus 로고
    • note
    • 5} moiety.
  • 66
    • 0002343287 scopus 로고
    • 1,1′-Bis(diphenylphosphino)ferrocene-Coordination Chemistry, Organic Syntheses, and Catalysis
    • Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, Chapter 1.2
    • Gan, K.-S.; Hor, T. S. A. 1,1′-Bis(diphenylphosphino)ferrocene- Coordination Chemistry, Organic Syntheses, and Catalysis. In Ferrocenes-Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; Chapter 1.2, pp 3-18.
    • (1995) Ferrocenes-Homogeneous Catalysis, Organic Synthesis, Materials Science , pp. 3-18
    • Gan, K.-S.1    Hor, T.S.A.2
  • 77
    • 33750304950 scopus 로고    scopus 로고
    • note
    • -3. CCDC: deposition no. 604813. The structure was solved and refined as indicated in Experimental Section with the following restraints: The different alkenyl moieties were refined as two independent contributing parts with the C(23) pivot atom. C(24a,b) and C(25a,b) were refined isotropically, the trans-component having fixed C(23)-C(24b) and C(24b)-C(25b) bond lengths. The refinement resulted in (E):(Z) occupancies in ca. 1:3 ratio. Phenyl ring carbons were refined over two positions with isotropic displacement parameters and geometry constrained to an ideal hexagon (C-C = 1.39 Å; the refinement converged to nearly 50:50 occupancies for both rings). In addition, several atom pairs from the complementary moieties were included in the model as having identical displacement parameters. All hydrogen atoms were included in calculated positions and refined using the riding model.
  • 78
    • 33750373508 scopus 로고    scopus 로고
    • note
    • The numerical values are given as follows: molecule 1 [molecule 2]. Where appropriate, we use generally defined parameters with variable indexes (n = 1 for molecule 1, n = 2 for molecule 2).
  • 79
    • 0035823850 scopus 로고    scopus 로고
    • The bond distance was retrieved from the Cambridge Structural Database. For the original reference, see: Harada J.; Ogawa, K. J. Am. Chent. Soc. 2001, 123, 10884-10888.
    • (2001) J. Am. Chent. Soc. , vol.123 , pp. 10884-10888
    • Harada, J.1    Ogawa, K.2
  • 83
    • 33750332849 scopus 로고    scopus 로고
    • note
    • The same applies to voltammetric waves observed at Pt-RDE.
  • 84
    • 33750299340 scopus 로고    scopus 로고
    • note
    • pa) shifts slightly to higher potentials upon raising the scan rate.
  • 87
    • 4944223882 scopus 로고    scopus 로고
    • 5(dppf-κP)] shows two successive oxidation at 0.34 V (ferrocene/ferrocenium, reversible) and 1.00 V (W-centered, irreversible) but with similar peak currents: Ohs, A. C.; Rheingold, A. L.; Shaw, M. J.; Nataro, C. Organometallics 2004, 23, 4655-4660.
    • (2004) Organometallics , vol.23 , pp. 4655-4660
    • Ohs, A.C.1    Rheingold, A.L.2    Shaw, M.J.3    Nataro, C.4
  • 90
    • 33750313810 scopus 로고    scopus 로고
    • note
    • pc. In the voltammogram recorded at RDE, the wave due to the ferrocene oxidation exerts the normal sigmoidal shape and a height corresponding to one electron exchanged while the third oxidation is observed as a tilted irreversible wave of approximately half-height of the first wave. The second wave from cyclic voltammogram is not reflected at all in the voltammogram at RDE.


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