S. Ye, W.K. Leong / Journal of Organometallic Chemistry 691 (2006) 1216–1222
1221
4.3. Reaction of CpRu(CO)2Cl and NaRe(CO)5
Acknowledgements
A solution of 2 (0.39 mmol) in THF (5 ml) was trans-
ferred onto CpRu(CO)2Cl (3c) (100 mg, 0.39 mmol). The
mixture was stirred at room temperature with the exclu-
sion of light in a Carius tube for 40 h. The precipitated
NaCl was then filtered off via cannula and the solvent
removed on the vacuum line. Column chromatographic
separation on silica, eluting with toluene/hexane (1:1,
v/v) afforded a yellow band of Cp(CO)2RuRe(CO)5 (4c)
(yield = 120 mg, 56.4%). Further elution with a toluene/
THF mixture afforded brown-red [CpRu(CO)2]2 (6)
(yield = 31.6 mg).
Compound 4c: IR (KBr): mCO 2103m, 2071w,
1997vs, 1977w, 1963w, 1931w. 1H NMR (C6D6): d
4.44 (s, 5H, Cp). FAB-MS (m/z): 549.8 (M+). Calcu-
lated for C12H5-O7ReRu: C, 26.19; H, 0.92. Found:
C, 25.93; H, 1.06%.
This work was supported by an A*STAR grant (Re-
search Grant No. 012 101 0035).
Appendix A. Supplementary material
Crystallographic data (excluding structure factors) for
the structures in this paper have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication numbers CCDC 286282–286286. Copies
of the data can be obtained, free of charge, on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax:
+44 1223 336 033 or e-mail: deposit@ccdc.cam.ac.uk).
Supplementary data associated with this article can be
References
4.4. Procedure for the catalytic runs
[1] (a) P. Braunstein, J. Rose, in: E.W. Abel, F.G.A. Stone, G. Wilkinson
(Eds.), Comprehensive Organometallic Chemistry II, vol. 10, Elsevier,
Oxford, 1995, p. 351;
In a typical run, acetic acid (68 ll, 1.0 mmol), phenyl-
acetylene (0.11 ml, 1.0 mmol) and the catalyst (0.01 mmol)
in toluene (1.0 ml) were stirred at 110 ꢁC for 24 h. After
cooling, the solution was concentrated by rotary evapora-
tion and then separated by column chromatography on sil-
ica gel (eluant: hexane–diethyl ether, 10:1, v/v) to afford a
mixture of the Z- and E-enol esters (0.14 g, colourless
oil), followed by the Markovnikov adduct. The ratios of
the products obtained were determined by integration of
(b) R.D. Adams, F.A. Cotton (Eds.), Catalysis by Di and Polynuclear
Metal Cluster Complexes, Wiley–VCH, New York, 1998;
(c) P. Braunstein, J. Rose, in: I. Bernal (Ed.), Chemical Bonds: Better
Ways to Make Them and Break Them, Elsevier, Amsterdam, 1989, p.
89;
(d) G. Suss-Fink, G. Meister, Adv. Organomet. Chem. 35 (1993) 41.
¨
[2] (a) D.W. Stephan, Coord. Chem. Rev. 95 (1989) 41;
(b) N. Wheatley, P. Kalck, Chem. Rev. 99 (1999) 3379;
(c) R.D. Adams, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.),
Comprehensive Organometallic Chemistry II, vol. 10, Elsevier,
Oxford, 1995, p. 1;
1
the H NMR spectrum after solvent removal but before
chromatographic separation.
(d) M.J. Chetcuti, in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.),
Comprehensive Organometallic Chemistry II, vol. 10, Elsevier,
Oxford, 1995, p. 24.
4.5. X-ray crystal structure determinations
[3] (a) C.D. Nunes, M. Pillinger, A. Hazell, J. Jepsen, T.M. Santos, J.
Madureira, A.D. Lopes, I.S. Goncalves, Polyhedron 22 (2003) 2799;
(b) F. Fagalde, M.G. Mellace, d.K. Lis, D. Noemi, N.E. Katz, J.
Coord. Chem. 57 (2004) 635.
[4] (a) A. Vogler, J. Kisslinger, Inorg. Chim. Acta 115 (1986) 193;
(b) S. Van Wallendael, D.P. Rillema, J. Chem. Soc., Chem. Commun.
(1990) 1081;
Diffraction quality crystals were grown by slow diffusion
of hexane or toluene onto THF solutions. Crystals were
mounted on quartz fibres. X-ray data were collected on a
Bruker AXS APEX system, using Mo Ka radiation, at
223 K with the SMART suite of programs [13]. Data were
processed and corrected for Lorentz and polarisation
effects with SAINT [14], and for absorption effects with SAD-
ABS [15]. Structural solution and refinement were carried
out with the SHELXTL suite of programs [16]. Crystal and
refinement data are summarised in Table 2.
The structures were solved by direct methods to locate
the heavy atoms, followed by difference maps for the
light, non-hydrogen atoms. The hydride in 4 was located
in a low angle difference map, and refined with a fixed
isotropic thermal parameter. All non-hydrogen atoms
were generally given anisotropic displacement parameters
in the final model. Organic hydrogen atoms were placed
in calculated positions and refined with a riding model.
Solvent molecules were found in 4a, 4b and 5, and the
THF molecule in 5 was disordered; appropriate restraints
were placed on the bond parameters of the disordered
solvent molecule.
(c) S. Van Wallendael, D.P. Rillema, Coord. Chem. Rev. 111 (1991)
297;
(d) M. Furue, M. Naiki, Y. Kanematsu, T. Kushida, M. Kamachi,
Coord. Chem. Rev. 111 (1991) 221;
(e) D.W. Thompson, J.R. Schoonover, T.J. Meyer, R. Argazzi, C.A.
Bignozzi, J. Chem. Soc., Dalton Trans. (1999) 3729;
(f) G. Albertin, S. Antoniutti, A. Bacchi, G.B. Ballico, E. Bordignon,
G. Pelizzi, M. Ranieri, P. Ugo, Inorg. Chem. 39 (2000) 3265;
(g) S. Encinas, F. Barigelletti, A.M. Barthram, M.D. Ward, S.
Campagna, J. Chem. Soc., Chem. Commun. (2001) 277;
(h) F. Fagalde, N.E. Katz, J. Coord. Chem. 54 (2001) 367;
(i) J.-L. Zuo, E. Herdtweck, F.E. Kuehn, J. Chem. Soc., Dalton
Trans. (2002) 1244;
(j) M.G. Mellace, F. Fagalde, N.E. Katz, Polyhedron 22 (2003) 369.
[5] (a) M. Cazanoue, Z. He, D. Neibecker, R. Mathieu, J. Chem. Soc.,
Chem. Commun. (1991) 307;
(b) Z. He, D. Neibecker, N. Lugan, R. Mathieu, Organometallics 11
(1992) 817;
(c) Z. He, S. Nefedov, N. Lugan, D. Neibecker, R. Mathieu,
Organometallics 12 (1993) 3837.
Ye, Suming
