Abstract
The diiron ynamine complex [Fe2(CO)7{μ-C(Ph)C(NEt2)}] (1) reacts with the diphenylbuta-1, 4-diyne, PhC≡C-C≡CPh, in refluxing hexane to yield three isomer complexes [Fe2(CO)6{C(Ph)C(NEt2)C(Ph)C(C2Ph}] (2a), [Fe2(CO)6{C(Ph)C(NEt2)C(C2Ph)C(Ph)}] (2b), and [Fe2(CO)6{NEt2)C(Ph)C(C2)C(Ph)}] (2c) All three compounds were identified by their1H NMR spectra. Compounds2a and2c were characterized by single crystal X-ray diffraction analyses. Crystal data: for2a: space group = P21/n,a = 17.873(1) Å,β = 18.388(6) Å,c = 9.429(3) Å β = 91.99(3)°,Z = 4.3751 reflections,R = 0.044; for2c: space group = P21/n,a = 40.58(2) å,b = 12.101(9) Å,c = 12.551(5) Å,β = 94.29(7)°,Z = 8.4723 reflection,R = 0.076. Complexes2a and2b result from a [2 + 2] cycloaddition between one of the C≡C triple bonds of the diyne ligand and the Fe≡C carbene bond, whereas2c results from insertion of one of the C≡C group into the bridging carbene. Addition of [Fe2(CO)9] on2a gave two major products, the tripledecker [Fe3(CO)8{C(Ph)C(NEt2)C(C2Ph)}], (3 and a tetrairon cluster [Fe4(CO)11{C(Ph)C(NEt2)C(Ph)C(C2Ph)}] (4). Both compounds were characterized by single crystal diffraction analyses. Crystal data: for3: space group = P21/n,a = 12.039(3) Å,b = 18.046(3) å,c = 15.270(2) Å,β = 90.11(2)°,Z = 4, 1430 reflections,R = 0.067; for4 space group = C2/c,a = 18.633(3) Å,b = 21.467(1)_Å,c = 20.742(2) Å,β = 115.03(8)°,Z = 8.992 reflections, R = 0.076. Complex4 is based on a “spiked” triangular cluster with the alkynyl triple bond attached inμ 3-parallel mode on the triangular grouping.
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References
E. Cabrera, J. C. Daran, Y. Jeannin, and O. Kristiansson (1986).J. Organomet. Chem. 310, 367; (B) R. D. Adams, J. C. Daran, and Y. Jeannin (1992).J. Cluster Sci. 3, 1.
B. Heim, J. C. Daran, Y. Jeannin, B. Eber, G. Huttner, and W. Imhof (1992).. Organomet. Chem. 310, 367.
V. Crocq (1989), Thesis. University of Paris VI.
E. Cabrera, J. C. Daran, and Y. Jeannin (1988).Organometallics 7, 2010.
J. F. Corigan, S. Doherty, N. J. Taylor, and A. J. Carty (1993).Organometallics 12, 1365; (b) J. F. Corrigan, S. Doherty, N. J. Taylor, and A. J. Carty (1992).Organometallics 11, 3160; (c) C. J. Adams, M. I. Bruce, E. Horn, and E. R. T. Tiekink (1992).J. Chem. Soc., Dalton Trans. 7, 1157; (d) G. H. Worth, B. H. Robinson, and J. Simpson (1992).Organometallics 11, 501; (e) M. I. Bruce, G. A. Koutsantonis, and E. R. T. Tiekink (1991).Inorg. Chim. Acta 34, 261; (g) K. H. Pannell and G. M. Crawford (1973).J. Coord. Chem. 2, 251.
R. B. King,in J. J. Eisch and R. B. King (eds.).Organometallic Syntheses, Vol. 1 (Academic Press, New York, 1965).
N. Walker and D. Stuart (1983).Acta Crystallogr. 39, 158.
D. J. Watkin, J. R. Carruthers, and P. W. Betteridge,CRYSTALS, An Advanced Crystallographic Program System (Chemical Crystallography Laboratory, University of Oxford, Oxford, England, 1986).
International Tables for X-ray Crystallography, Vol. IV (Kynoch Press, Birmingham, England, 1974).
G. M. Sheldrick,SHELXS 86, Program for Crystal Structure Solution (University of Göttingen, Göttingen, Germany, 1986).
E. Prince,Mathematical Techniques in Crystallography (Springer-Verlag, Berlin, 1982).
W. P. Felhammer and H. Stolzenberg,in G. Wilkinson, F. G. A. Stone, and E. Abel (eds.).Comprehensive Organometallic Chemistry, Chap 31.4 (Pergamon, Oxford, 1982).
K. Nakanishi,Infrared Absorption Spectroscopy (Holden-Day, San Francisco and Nankodo Company Limited, Tokyo, 1962).
D. P. Mingos and D. J. WalesIntroduction to Cluster Chemistry (Print-Hall International, Englewood Cliffs, New Jersey, 1990).
B. Eber, G. Huttner, C. Emmerich, J. C. Daran, B. Heim, and Y. Jeannin (1991).Organomet. Chem. 419, 43.
K. Hoffman and E. Weiss (1977).J. Organomet. Chem. 128, 237.
R.D. Adams, G. Chen, J. T. Tanner, and J. Yin (1990).Organometallics 9, 595.
E. Cabrera, J. C. Daran, and Y. Jeannin (1989).Organometallics 8, 1811.
B. Heim (1992). Thesis, University of Paris VI.
J. C. Daran, B. Heim, and Y. Jeannin (1991).C.R. Acad. Sci. Paris 312, 1117.
M. Gouygou, J. C. Daran, B. Heim, and Y. Jeannin (1993).J. Organomet. Chem. 460, 219
V. Crocq, J. C. Daran, and Y. Jeannin (1989).J. Organomet. Chem. 373, 85.
J. C. Daran, M. Gouygou, B. Heim, and Y. Jeannin,J. Organomet. Chem. (in press).
R. P. Dodge and V. Schomaker (1965).J. Organomet. Chem. 3, 247; (b) D. Nuel, F. Dahan, and R. Mathieu (1985).J. Am. Chem. soc. 107, 1658.
R. D. Adams, G. Chen, S. Sun, J. T. Tanner, and T. A. Wolfe (1990).Organometallics 9, 251.
E. Sappa, A. Tiripicchio, and P. Braunstein (1983).Chemical Review 83, 204; (b) S. Rivomanana, G. Lavigne, N. Lugan, and J. J. Bonnet (1991).Organometallics 10, 2285.
D. Osella, L. Pospisil, and J. Fiedler (1993).Organometallics 12, 3140; (b) J. F. Halet, J. Y. Saillard, R. Lissillour, M. J. McGlinchey, and G. Jaouen (1985).Inorg. Chem. 24, 218; (c) K. Wade,in B. F. G. Johnson (ed),Transition-Metal Cluster (Wiley, New York, 1980), p. 143.
D. Nuel, f. Dahan, and R. Mathieu (1985).Organometallics 4, 1436.
D. Lentz and M. Reuter (1991).Chem. Ber. 124, 773; (b) ibid. (1992).Z. Anorg. Allg. 1980), p. 143.
R. Rumin, F. Petillon, L. Manojlovic-Muir, and K. W. Muir (1990). Organometallics9, 944.
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Daran, J.C., Gilbert, E., Gouygou, M. et al. Coupling insertion reactions of diphenylbuta-1, 4-diyne into iron-carbene bonds of [Fe2(CO)7{μ-C(Ph)C(NEt2}]. Syntheses and reactivities of the ferracyclopentadiene [Fe2(CO)6{C(Ph)C(NEt2)C(Ph)C(C2Ph)}] with [Fe2(CO)9]. J Clust Sci 5, 373–400 (1994). https://doi.org/10.1007/BF01379056
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DOI: https://doi.org/10.1007/BF01379056