Abstract
An overview of the work performed at the University of Turin in the last 25 years on the reactivity of Ru3(CO)12 with alkynes and related reactions is given. An outline of the history of the beginning of this chemistry and of its developments (seen under a personal point of view) is followed by attempts at drawing some general conclusions and making come comments on the present state-of-the-art in different field of this research. Our results are compared with those of several other researchers working on the same chemistry. An outline of the potentiality of ruthenium-based clusters as models of intermediates in organic syntheses and in homogeneous catalysis is also given.
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References
W. Reppe et al. (1953).Liebigs Ann. Chem. 582, 1, 38, 72, 87, 116, 133.
(a) M. Reza-Pahlevi (1973), “Oil is not forever”: (b) R. Khomeini (1979. “Do oil and turmoil mix?”; (c) S. Hussein (1990). “Arabian ‘light’.”
R. J. Tedeschi,Acetylene-based Chemicals from Coal and Other Natural Resources (M. Dekker, New York, 1983).
See for example: (a) Y. Shvo, 8th International Symposium on Homogeneous Catalysis, Amsterdam. Aug. 2–7, 1992. paper 1–16; (b) F. M. Menger, S. Brocchini, and X. Chen (1992).Angew. Chem. Int. Ed. Ed. Engl. 31, 1492.
G. P. Chiusoli, M. Costa, and C. Pelizzi (1990)14 465, and refereces therein
A. Wojcicki and C.F. Schubart (1990). Coord. Chem. Rev105, 35.
See for example: (a) J. S. Moore, C. G. Gorman, and R. H. Grubbs (1991),J. Am. Chem. Soc. 113 1704; J. Zhang and J. S. Moore (1992),J. Am. Chem. Soc. 114, 9701; (b) Y. Rubin, C. B. Knobler, and F. Diederich (1991).Angew. Chem. Int. Engl. 30 698; (c) V. Parasuk, J. Almlöf, and M. W. Feyereisen (1991).J. Am. Chem. Soc. 113, 1049; (d) A. M. Boldi, J. Anthony, C. B. Knobler, and F. Diederich (1992).Angew. Chem. Int. Ed. Engl. 31, 1240; (e) J. S. Moore and J. Zhang (1992).Angew. Chem. Int. Ed. Engl. 1101–1264; (g) R. Corriu, P. Gerbier, C. Guérin, and B. Henner (1992).Angew. Chem. 31, 1195; (h) M. S. Paley, D. O. Frazier, H. Abeledeyem, S. P. McManus, and S. E. Zutaut (1992).J. Am. Chem. Soc. 114, 3247; (i) R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, and K. P. C. Vollhardt (1992),Angew. Chem. Int. Ed. Engl. 31, 1643; (j) I. Bunz, K. P. C. Vollhardt, and J. S. Ho (1992).Angew. Chem. Int. Ed. Engl. 31, 1648.
M. W. Geis and J. C. Angus (1992)Scientific American, p. 64.
See for example: (a) K. C. Nicolau and W.-M. Dai (1991),Angew. Chem. Int. Ed. Engl. 30, 1387–1530; (b) K. C. Nicolaou, P. Maligres, T. Suzuki, S. V. Wenderborn, W. M. Dai, and R. K. Chadha (1992).J. Am. Chem. Soc. 114, 8890; (c) K. C. Nicolaou and W. M. Dai (1992).J. Am. Chem. Soc. 114, 8908.
E. L. Muetterties (1975),Bull. Soc. Chim. Belg. 84, 953; idem (1976). ibidem, 85,451; (b) E. L. Muetterties, T. N. Rhodin, E. Band, C. F. Brucker, and W. R. Pretzer (1979).Chem. Rev. 79, 91.
(a) Iron: W. Hübel,in L. Wender and P. Pino (eds.),Organic Syntheses via Metal Carbonyls, Vol. 1 (J. Wiley Interscience, New York, 1968), p. 273; (b) Cobalt; R. F. Heck, ibidem, Vol. I, p. 373.
Iron: (a)_J. F. Blount, L. F. Dahl, C. Hoogzand, and W. Hübel (1966),J. Am. Chem. Soc. 88, 292; (b) R. P. Dodge and V. Shomaker (19675).J. Organomet. Chem. 3, 274; Cobalt: (c) L.F. Dahl and D. L. Smith (1962).J. Am. Chem. Soc. 84, 2450; (d) P. Chini and B. T. Heaton (1977).Tropics Curr. Chem. 77 1.
G. Cetini, O. Gambino, E. Sappa and G. A. Vaglio (1966-67)Atti. Acc. Sci. Torino 101, 855; (b) G. Celini, O. Gambino, E. Sappa, and G. A. Vaglio (1967).Ric. Sci. 37. 430; (c) G. Cetini, O. Gambino, R. Rossetti, and E. Sappa (1967),J. Organomet. Chem. 8, 149.
G. Cetini, O. Gambino, E. Sappa, and M. Valle (1969),J. Organomet. Chem. 17, 437.
B. F. G. Johnson, J. Lewis, B. E. Reichert, K. T. Schorpp, and G. M. Sheldrick (1977),J. Chem. Soc. Dalton Trans. 1417.
E. Sappa and L. Milone (1973), J. Organomet. Chem.61, 383.
See for example; (a) S. Cenini, M. Pizzotti, and C. Crotti,in R. Uego (ed.),Aspects of Homogeneous Catalysis, Vol. 6 (Reidel, Dordrecht, 1988), p. 97; (b) C. Crotti, S. Cenini, A. Bassoli, B. Rindone, and F. Demartin (1991),J. Mol. Catal. 70, 175; (c) S. Bhaduri, K. S. Gopalkrishnan, G. M. Shedrick, W. Clegg and D. Stalke (1983).J. Chem. Soc. Dalton Trans. 2339; (d) A. Basu, S. Bhaduri, and H. Khwaja (1987).J. Organomet. Chem. 319, C 28: (e) S. Bhaduri, H. Khwaja, N. Sapre, K. Sharma, A. Basu, P. G. Jones, and G. Carpenter (1990),J. Chem. Soc. Dalton Trans. 1313; (f) J. A. Smieja and W. L. Gladfelter (1986).Inorg. Chem. 25, 2667; (g) S.-H. Han, G. L. Geoffroy, and A. L. Rheingold (1987).Inorg. Chem. 26, 3426; (h) S.-H. Han and W. L. Geoffroy (1988).Polyhedron 7, 2331; (i) J.-S. Song, S.-H. Han, S. T. Nguyen, G. L. Geoffroy, and A. L. Rheingold (1990).Organometallics 9, 2386.
E. Sappa, O. Gambino, and G. Cetini (1972),J. Organomet. Chem. 35, 375.
A. J. Deeming, R. Ettore, B. F. G. Johnson, and J. Lewis (1971).J. Chem. Soc. (A) 1797.
O. Gambino, E. Sappa, and G. Cetini (1972).J. Organomet. Chem. 44, 185.
E. Sappa, A. Tiripicchio, and P. Braunstein (1983),Chem. Rev. 83, 203; (b) E. Sappa, A. Tiripicchio, and P. Braunstein (1985),Coord. Chem. Rev. 64, 219; (c) J.-F. Halet, J. Y. Saillard, R. Lissillour, M. J. McGlinchey, and G. Jaouen (1985),Inorg. Chem. 24, 218; (d) F. W. B. Einstein, K. G. Tyers, A. S. Tracey, and D. Sutton (1986),Inorg. Chem. 25, 1631.
R. Giordano and E. Sappa (1993),J. Organomet. Chem. 448, 157.
D. Cauzzi, R. Giordano, E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1993),J. Cluster Sci. 4, 279.
E. Sappa, L. Milone, O. Gambino, and G. Cetini (1972),J. Organomet. Chem. 39, 169.
M. Catti, G. Gervasio, and S. A. Mason (1977),J. Chem. Soc. Dalton Trans. 2260, and references therein.
M. Evans, M. Hursthouse, E. W. Randall, E. Rosenberg, L. Milone, and M. Valle (1972).J. Chem. Soc. Chem. Commun. 545.
G. Gervasio, D. Osella, and M. Valle (1976),Inorg. Chem. 15, 1221.
M. Castiglioni, L. Milone, D. Osella, G. A. Vaglio, and M. Valle (1975),Inorg. Chem. 15, 394.
O. Gambino, E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1979),Inorg. Chim. Acta 36, 189.
E. Rosenberg, S. Aime, L. Milone, E. Sappa, A. Tiripicchio, and A. M. Manotti Lanfredi (1981).J. Chem. Soc. Dalton Trans. 2023.
E. Sappa, L. Milone, and A. Tiripicchio (1976).J. Chem. Soc. Dalton Trans. 1843.
S. Aime, L. Milone, E. Sappa, and A. Tiripicchio (1977),J. Chem. Soc. Dalton Trans. 227.
E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1978).J. Chem. Soc. Dalton Trans. 419.
S. Aime, G. Nicola, D. Osella, A. M. Manotti Lanfredi, and A. Tiripicchio (1984).Inorg. Chim. Acta 85, 161.
H. Vahrenkamp and E. J. Wucherer (1981.Angew. Chem. Int. Ed. Engl. 20, 680; (b) H. Vahrenkamp and D. Wolters (1982).Organometallics 1, 874; (c) H. Vahrenkamp and D. Wolters (19082),J. Organomet. Chem. 224, C 17.
E. Sappa, A. Tiripicchio, and A. M. Manotti Lanfredi (1978).J. Chem. Soc. Dalton Trans. 552.
O. Gambino, G. A. Vaglio, R. P. Ferrari, and G. Cetini (1971),J. Organomet. Chem. 30, 381.
G. Ferraris and G. Gervasio (1972).J. Chem. Soc. Dalton Trans. 1057; G. Ferraris and G. Gervasio (1974).J. Chem. Soc. Dalton Trans. 1813.
See for example: B. F. G. Johnson, R. Khattar, J. Lewis, and P. R. Raithby (1987),J. Organomet. Chem. 335, C 17, and references therein.
C. G. Pierpont (1977).Inorg. Chem. 16, 636.
M = Os: (a) J.A. Clucas, P. A. Dolby, M. M. Harding, and A. K. Smith (1987),J. Chem. Soc. Chem. Commun. 1829; R = Ru; (b) S. Rivomanana, G. Lavigne, N. Lugan, and J.-J. Bonnet (1991).Inorg. Chem. 30, 4110.
V. Busetti, G. Granozzi, S. Aime, R. Gobetto, and D. Osella (1984).Organometallics 3, 1510.
J. Lewis, A. D. Massey, M. Monari, B. F. G. Johnson, D. Braga, and F. Grepioni (1992).J. Chem. Soc. Dalton Trans. 249.
J. J. Schneider, M. Nolte, and C. Krüger (1991).J. Organomet. Chem. 403, C 4.
A. J. Carty, N. J. Taylor, E. Sappaq, A. Tiripicchio, and M. Tiripicchio Camellini (1991).Organometallics 10, 1907.
M. E. Garcia, J. C. Jeffery, P. Sherwood, and F. G. A. Stone (1987).J. Chem. Soc. Dalton Trans. 1209.
L. Busetto, J. C. Jeffery, R. M. Mills, F. G. A. Stone, M. J. Went, and P. Woodward (1983).J. Chem. Soc. Dalton Trans. 101.
G. A. Koutsantonis, J. P. Selegue, and J.-G. Wang (1992).Organometallics 11, 2704.
(a) S. Aime, L. Milone, E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1979).J. Chem. Soc. Dalton Trans. 1155; (b) A. J. Carty, N. J. Taylor, and E. Sappa (1988).Organometallics 7, 405.
K. Wade (1976).Adv. Inorg. Chem. Radiochem. 18, 1; (b) D. M. P. Mingos (1984).Acc. Chem. Res. 17, 311.
D. Osella R. Gobetto, P. Montangero, P. Zanello, and A. Cinquantini (1986).Organometallics 5, 1247; (b) B. E. R. Schilling and R. Hoffmann (1979).J. Am. Chem. Soc. 101, 3456; (c) G. Granozzi, E. Tondello, M. Casarin, S. Aime, and D. Osella (1983).Organometallics 2, 430.
D. Osella, L. Pospisil and J. Fiedler (1993)Organometallics 12, 3140.
E. Sappa (1987).J. Organomet. Chem. 323, 83.
J. S. Bradley (1983).Adv. Organomet. Chem. 22, 1.
S. Rivomanana, G. Lavigne, N. Lugan, J.-J. Bonnet, R. Yanez, and R. Mathieu (1989),J. Am. Chem. Soc. 111, 8959.
S. Rivomanana, G. Lavigne, N. Lugan, and J.-J. Bonnet (1991),Organometallics 10, 2285.
D. Nuel, F. Dahan, and R. Mathieu (1985).Organometallics 4, 1436.
G. Lavigne, N. Lugan, S. Rivomanana, F. Mulla, J. M. Soulié, and P. Kalck (1993),J. Cluster Sci. 4, 49.
E. Sappa and A. Tiripicchio (1988).New J. Chem. 12, 599.
H. Vahrenkamp (1983).Adv. Organomet. Chem. 22, 169.
E. Sappa, D. Belletti, A. Tiripicchio, and M. Tiripicchio Camellini (1989),J. Organomet. Chem. 359, 419.
M. Lanfranchi, A. Tiripicchio, M. Tiripicchio Camellini, O. Gambino, and E. Sappa (1982).Inorg. Chim. Acta 64, L 269.
M. L. Nanni Marchino, E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1984).J. CHem. Soc. Dalton Trans. 1541.
A. Sironi, G. Gervasio, and E. Sappa, manuscript in preparation.
E. Sappa, A. M. Manotti Lanfredi, G. Predieri, A. Tiripicchio, and A. J. Carty (1985).J. Organomet. Chem. 288, 365, and references therein.
M. Lanfranchi, A. Tiripicchio, E. Sappa, S. A. MacLaughlin, and A. J. Carty (1982).J. Chem. Soc. Chem. Commun. 538.
F. G. A. Stone (1984).Angew. Chem. Int. Ed. Engl. 23, 89; see also: (b) G. P. Elliott, J. A. K. Howard, T. Mise, C. M. Nunn, and F. G. A. Stone (1986),Angew. Chem. Int. Ed. Engl. 25, 190, and references therein.
E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1979).J. Chem. Soc. Chem. Commun. 254.
A. J. Carty, N. J. Taylor, E. Sappa, and A. Tiripicchio (1983).Inorg. Chem. 22, 1871.
A. Tiripicchio, M. Tiripicchio Camellini, and E. Sappa (1984),J. Chem. Soc. Dalton Trans. 627.
R. Hoffmann (1982).Angew. Chem. Int. Ed. Engl. 21, 711.
A discussion of the synthetic procedures for—and the structures of—these complexes if in: (a) G. Gervasio, R. Giordano, E. Sappa, M. Costa, G. Predieri, and A. Tiripicchio (1993).J. Cluster Sci. 4, 33; A more detailed discussion of the syntheses will be given in a forthcoming paper; (b) E. Sappa, G. Predieri, and a Tiripicchio, in preparation.
S. Aime and A. J. Deeming (1981).J. Chem. Soc. Dalton Trans. 828.
S. Ermer, R. Karpelus, S. Miura, E. Rosenberg, A. Tiripicchio, and A. M. Manotti Lanfredi (1980).J. Organomet. Chem. 187, 81.
E. Sappa and G. Predieri, manuscript in preparation.
S. Aime and E. Sappa, manuscript in preparation.
S. Aime, A. J. Deeming, M. B. Hursthouse, J. D. J. Baker-Dirks (1982).J. Chem. Soc. Dalton Trans. 1625.
H. Berke, U. Grössman, G. Huttner, and L. Zsolnai (1984).Chem. Ber. 117, 3432.
E. Sappa, G. Predieri, and A. Tiripicchio, manuscript in preparation.
G. Gervasio and E. Sappa (1993).Organometallics 12, 1458.
L. Milone, D. Osella, M. Ravera, P. L. Stanghellini, and E. Stein (1992).Gazz. Chim. Ital. 122, 451.
(a) S. Aime, L. Milone, and D. Osella (1979).J. Chem. Soc. Chem. Commun. 704; (b) S. Aime, L. Milone, D. Osella, A. Tiripicchio, and A. M. Manotti Lanfredi (1982).Inorg. Chem. 21, 501; (c) S. Aime, D. Osella, L. Milone, A. M. Manotti Lanfredi, and A. Tiripicchio (1983).Inorg. Chim. Acta 71, 141; (d) S. Aime, D. Osella, L. Milone, and A. Tiripicchio (1983).Polyhedron 2, 77.
J. M. Basset and A. Choplin (1983).J. Mol. Cat. 21, 95.
R. Gobetto, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, and M. J. Mays (1990).J. Chem. Soc. Dalton Trans. 807.
E. Sappa, A. Tiripicchio, and M. J. Mays, in preparation.
A. Wojcicki (1993).J. Cluster Sci. 4, 59.
(a) S. Aime, D. Osella, A. J. Aree, A. J. Deeming, M. B. Hursthouse, and A. M. R. Galas (1984).J. Chem. Soc. Dalton Trans.; (b) S. Aime, D. Osella, A. J. Deeming, A. J. Aree, M. B. Hursthouse, and H. M. Dawes (1986).J. Chem. Soc. Dalton Trans. 1459.
S. Aime, G. Jannon, D. Osella, and A. J. Deeming (1981).J. Organomet. Chem. 214, C 15.
R. A. Flinn, O. A. Larson, and H. Beuther (1963). Hydrocarbon Process.Pet. Refiner 9, 129; (b) C. N. Satterfieldet al. (1976).Ind. Eng. Chem., Proc. Des. Div. 15 272; (1981).20, 538; (1981).20, 62; (1981).19, 153; (c) F. E. Massoth, K. Balusami, and J. Shabtai (1990).J. Catal. 122, 256; (d) E. O. Odebunmi and D. F. Oliis (1983).J. Catal. 80, 76. (e) S. Eijsbouts, V. H. J. deBeer, and R. Prins (1990).J. Catal. 127, 619.
R. M. Laine, D. W. Thomas, and L. W. Cary (1979).J. Org. Chem. 44, 4964; Idem: (1982),J. Am. Chem. Soc. 104, 1763, (c) F. E. Massoth, K. Balusami, and J. Shabtai (1990).J. Catal. 122, 256; (d) E. O. Odebunmi and D. F. Oliis (1983).J. Catal. 80, 76. (e) S. Eijsbouts, V. H. J. deBeer, and R. Prins (1990).J. Catal. 127, 619.
R. M. Laine, D. W. Thomas, and L. W. Cary (1979).J. Org. Chem. 44, 4964; Idem: (1982).J. Am. Chem. Soc. 104, 1763, (c) R. M. Laine (1987).New J. Chem. 11, 5113; (d) R. M. Laine (1985).Ann. N.Y. Acad. Sci. 415, 271; (e) R. M. Laine (1983).Catal. Rev. Sci. Eng. 25, 459; (f) R. H. Fish (1983).Ann. N.Y. Acad. Sci. 415, 292; (g) R. H. Fish, A. D. Thormodesen, and J. L. Tan (1984).J. Org. Chem. 49, 4500; (h) R. H> Fish, A. D. Thormodesen, and G. A. Cremer.J. Am. Chem. Soc. 104, 4500; (i) R. H. Fish, H.-S. Kim, J. E. Babin, and R. D. Adams (1988).Organometallics 7, 2250.
Ruthenium: M. Day, S. Hajela, K. I. Hardcastle, T. McPhillips, E. Rosenberg, M. Botta, R. Gobetto, L. Milone, D. Osella, and R. W. Gellert (1990).Organometallics,9, 913, and references therein; (b) Osmium: M. W. Day, S. Hajela, S. E. Kabir, M. irving, T. McPhillips, E. Wolf, K. I. Hardcastle, E. Rosenberg, L. Milone, R. Gobetto, and D. Osella (1991).Organometallics 10, 2743, and references therein; (b) E. Rosenberg, W. Freeman, Z. Carlos, K. I. Hardcastle, Y. J. Yoo, L. Milone, and R. Gobetto (1992).J. Cluster Sci. 3, 439.
D. M. Skinner, E. Rosenberg, J. Bracker-Novak, S. Aime, D. Osella, R. Gobetto, and L. Milone (1988).Organometallics 7, 856.
D. Nuel and R. Mathieu (1988).Organometallics 7, 16; (b) J. Suades, F. Dahan, and R. Mathieu (1988).Organometallics 7, 47.
G. Predieri, A. Tiripicchio, M. Tiripicchio Camellini, M. Costa, and E. Sappa (1990).Organometallics 9, 1729.
L. P. Battaglia, D. Delledonne, M. Nardelli, G. Predieri, G. P. Chiusoli, M. COsta, and C. Pelizzi (1989).J. Organomet. Chem. 363, 209.
G. Predieri, A. Tiripicchio, M. Tiripicchio Camellini, M. Costa, and E. Sappa (1992).J. Organomet. Chem. 423, 129.
G. Gervasio, E. Sappa, and L. Marko (1993).J. Organomet. Chem. 444, 203.
E. Sappa and G. Gervasio, unpublished results.
For analogous reactions on nickel see: (a) A. Furlani, P. Bicev, S. Franzoso, A. Chiesi Villa, A. Gaetani Manfredotti, and C. Guastini (1977).J. Chem. Soc. Perkin Trans. II, 1011; (b) P. Bicev, A. Furlani, and G. Sartori (1973).Gazz. Cim. Ital. 103, 849; (c) M. V. Russo and A. Furlani (1976).Tetrahedron Lett. 30, 2655; (d) A. Furlani, P. Bicev, M. V. Russo, and M. Fiorentino (1977).Gazz. Chim. Ital. 107, 373; (e) A. Furlani, M. V. Russo, and P. Bicev (1977).Gazz. Chim. Ital. 107, 517; (f) P. Carusi, G. Cerichelli, A. Furlani, M. V. Russo, and L. Subert (1987).Appl. Organomet. Chem. 1, 555; (g) A. Furlani, K. H. Hornemann, M. V. Russo, A. Chiesi Villa, and C. Guastini (1987).Gazz. Chim. Ital. 17, 429; (h) E. Andoni, M. Bossa, P. Carusi, C. Cauletti, and A. Furlani (1986).J. Mol. Struct. 140, 115; (i) A. Furlani and M. V. Russo (1990).Appl. Organomet. Chem. 4, 319.
S. A. R. Knox (1992),J. Cluster Sci. 3, 385, and references therein. (b) L. A. Brady, A. F. Dyke, S. E. Garner, S. A. R. Knox, A. Irving, S. M. Nicholls, and A. G. Orpen (1993).J. Chem. Soc. Dalton Trans. 487.
R. D. Adams, J. E. Babin, M. Tasi, and J. G. Wang (1988),Organometallics 7, 755.
S. Aime, L. Milone, E. Sappa, A. Tiripicchio, and A. M. Manotti Lanfredi (1979).J. Chem. Soc. Dalton Trans. 1664.
Formation of tropones from iron-ferroles is discussed in Ref. 72a. A comparable reaction sequence for di-iron derivatives, also leading to tropones is in: G. Hoghart, F. Kayser, S. A. R. Knox, D. A. V. Morton, A. G. Orpen, and M. L. Turner (1988).J. Chem. Soc. Chem. Commun. 358.
E. Boroni, M. Costa, G. Predieri, E. Sappa, and A. Tiripicchio (1992).J. Chem. Soc. Dalton Trans. 2585.
The structure of35 should be compared with that of the iron complex5; Fig. 2.
E. Sappa, D. Cauzzi, G. Predieri, and C. Vignali (1993).Spectrochim. Acta 49A, 1395.
M. Careri, G. Mori, G. Predieri, N. Souza de Rezende, and E. Sappa (1993).J. Chromatog. 634, 143; For a review on HPLC applied to clusters see; (b) A. Casoli, A. Mangia, G. Predieri, E. Sappa, and M. Volante (1989).Chem. Rev. 89, 407.
M. Careri, A. Mangia, P. Manini, G. Predieri, V. Raverdino, G. Tsoupras, and E. Sappa (1993).J. Chromatog. 647, 79.
Mass spectrometric studies on clusters, including new techniques, are in: A. Marinetti and E. Sappa (1981).Ann. Chim. 81, 707, and references therein.
C. Barner-Thorsen, K. I. Hardcastle, E. Rosenberg, J. Siegel, A. M. Manotti Lanfredi, A. Tiripicchio Camellini (1981).Inorg. Chem. 20, 4306.
P. Braunstein, G. Predieri, A. Tiripicchio, and E. Sappa (1982).Inorg. Chim. Acta 63, 113.
[Cu], R. A. Brice, S. C. Pearse, I. D. Salter, and K. Henrick (1986).J. Chem. Soc. Dalton Trans,2181, (b) [Ag], T. Adatia, M. McPartlin, and I. D. Salter (1988).J. Chem. Soc. Dalton Trans. 2889.
R. Fahmy, K. King, E. Rosenberg, A. Tiripicchio, and M. Tiripicchio Camellini (1980).J. Am. Chem. Soc. 102, 3626; (b) S. Ermer, K. King, K. I. Hardcastle, E. Rosenberg, A. M. Manotti Lanfredi, A. Tiripicchio, and M. Tiripicchio Camellini (1983).Inorg. Chem. 22, 1339; (c) E. Rosenberg, J. Wang, and R. W. Gellert (1988).Organometallics 7, 1093; (d) S. Hajela, B. M. Novak, and E. Rosenberg (1989).Organomettals 8, 468; (e) E. Rosenberg, K. I. Hardcastle, M. W. Day, R. Gobetto, S. Hajela, and R. Muftikian (1991).Organometallics 10, 203.
D. Osella, L. Milone, S. V. Kukharenko, V. V. Strelets, E. Rosenberg, and S. Hajela (1993).J. Organomet. Chem. 451, 153.
S. Aime, L. Milone, E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1979).Inorg. Chim. Acta 32, 163.
C. Jangala, E. Rosenberg, D. Skinner, S. Aime, L. Milone, and E. Sappa (1980).Inorg. Chem. 19, 1571; (b) A. J. Carty, S. A. MacLaughlin, N. J. Taylor, and E. Sappa (1981).Inorg. Chem. 20, 4437.
G. Predieri, A. Tiripicchio, C. Vignali, and E. Sappa (1988).J. Organomet. Chem. 342, C 33.
E. Sappa, G. Predieri, A. Tiripicchio, and C. Vignali (1989).J. Organomet. Chem. 378, 109.
E. Sappa, G. Predieri, A. Tiripicchio, and M. Tiripicchio Camellini (1985).J. Organomet. Chem. 297. 103.
R. Giordano, E. Sappa, and G. Predieri (1988). IVth European Symposium on Inorganic Chemistry, Freibourg (Germany), Sept. 12–15, Com. A4.
E. Sappa (1988).J. Organomet. Chem. 352, 327.
S. Aime, M. Botta, R. Gobetto, D. Osella, and L. Milone (1987).Gazz. Chim. Ital. 117, 773; S. Aime, R. Gobetto, G. Jannon, and D. Osella (1986).J. Organomet. Chem. 309, C 51; S. Aime, M. Botta, R. Gobetto, and D. Osella (1987).J. Organomet. Chem. 320, 229.
D. Osella, personal communication.
C. Weatherell, N. J. Taylor, A. J. Carty, E. Sappa, and A. Tiripicchio (1985).J. Organomet. Chem. 291, C 9.
P. Ewing and L. J. Farrugia (1989).Organometallics 8, 1246; (b) L. J. Farrugia (1990).Organometallics 9, 105.
A. J. Dent, L. J. Farrugia, A. G. Orpen, and S. E. Stratford (1992).J. Chem. Soc. Chem. Commun. 1456.
A. J. Farrugia, N. MacDonald, and R. D. Peacock (1991).J. Chem. Soc. Chem. Commun. 163.
G. G. Gervasio, S. Aime, L. Milone, E. Sappa, and M. Franchini Angela (1976).Transit. Met. Chem. 1, 96; (b) S. Aime, G. Gervasio, L. Milone, E. Sappa, and M. Franchini Angela (1978).Inorg. Chim. Acta 26, 145.
E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1980).Inorg. Chim. Acta 42, 255.
E. Sappa, A. M. Manotti Lanfredi, G. Predieri, and A. Tiripicchio (1982).Inorg. Chim. Acta 61, 217.
G Gervasio, E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1963).Inorg. Cim. Acta 68, 171.
E. Sappa, G. Pasquinelli, A. Tiripicchio, and M. Tiripicchio Camellini (1989).J. Chem. Soc. Dalton Trans. 601.
L. J. Farrugia (1992).J. Cluster Sci. 3, 361.
E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1978),Inorg. Chim. Acta 36, 197.
S. Aime, G. Gervasio, L. Milone, E. Sappa, M. Franchini Angela (1978).Inorg. Chim. Acta 26, 223; (b) C. Barner-Thornsen, E. Rosenberg, G. Saatjian, S. Aime, L. Milone, and D. Osella (1981).Inorg. Chem. 20, 1592.
A. J. Carty (1982).Pure & Appl. Chem. 53, 113; (b) A. J. Carty (1982).Adv. Chem. Ser. N. 196, 163.
A. J. Carty, S. A. MacLaughlin, and N. J. Taylor (1981).J. Organomet. Chem. 204, C 27.
S. A. MacLaughlin, J. P. Johnson, N. J. Taylor, A. J. Carty, and E. Sappa (1983).Organometallics 2, 352.
A. A. Cherkas, A. J. Carty, E. Sappa, M. A. Pellinghelli, and A. Tiripicchio (1987).Inorg. Chem. 26, 3201; (b) A. A. Cherkas, N. Hadj-Bagheri, A. J. Carty, E. Sappa, M. A. Pellinghelli, and A. Tiripicchio (1990).Organometallics 9, 1887.
D. Nucciarone, S. A. MacLaughlin, N. J. Taylor, and A. J. Carty (1988).Organometallics 7, 106.
D. Nucciarone, N. J. Taylor, A. J. Carty, A. Tiripicchio, M. Tiripicchio Camellini, and E. Sappa (1988).Organometallics 7, 118.
D. Nucciarone, N. J. Taylor, and A. J. Carty (1986).Organometallics 5, 1179.
S. M. Breckenridge, A. J. Carty, E. Sappa, M. A. Pellinghelli, and A. Tiripicchio, manuscript in preparation.
S. M. Breckenridge, N. J. Taylor, and A. J. Carty (1991).Organometallics 10, 837; (b) S. M. Randall, N. J. Taylor, A. J. Carty, T. Ben Haddah, and P. H. Dixneuf (1988).J. Chem. Soc. Chem. Commun. 870; (c) S. M. Breckenridge, N. J. Taylor, A. J. Carty, E. Sappa, M. A. Pellinghelli, and A. Tiripicchio, manuscript in preparation.
M. Castiglioni, G. Gervasio, and E. Sappa, (1981).Inorg. Chim. Acta 49, 217.
M. Castiglioni, R. Giordano, and E. Sappa (1983).J. Organomet. Chem. 258, 217.
M. Castiglioni, R. Giordano, and E. Sappa (1984).J. Organomet. Chem. 275, 119.
E. Sappa, A. M. Manotti Lanfredi, and A. Tiripicchio (1981).J. Organomet. Chem. 221, 93.
C. Bergounhou, J.-J. Bonnet, G. Lavigne, F. Papageorgiou, S. G. Shore, and U. Siriwardane (1989),Inorg. Synth. 26, 360.
S. G. Shore, W. L. Hsu, C. R. Weisenberger, M. L. Caste, M. R. Churchill, and C. Bueno (1982).Organometallics,1, 1405.
G. Lavigne, F. Papageorgiou, C. Bergounhou, and J.-J. Lanfranchi, and A. Tiripicchio (1983).J. Organomet. Chem. 241, 99; (b) See also: E. Sappa, M. Valle, S. G. Shore, and U. Siriwardane (1989),Inorg. Synth. 26, 365.
E. Sappa, M. Valle, G. Predieri, and A. Tiripicchio (1984).Inorg. Chim. Acta 88, L 23; (b) E. Sappa, M. L. Nanni Marchino, G. Predieri, A. Tiripicchio, and M. Tiripicchio Camellini (1986).J. Organomet. Chem. 307, 97.
[Au]: (a) P. Braunstein, J. Rosé, A. M. Manotti Lanfredi, A. Tiripicchio, and E. Sappa (1984).J. Chem. Soc. Dalton Trans. 1843; [Cu]: See Ref. 188; [Hg]: (b) G. Predieri, A. Tiripicchio C. Vignali, E. Sappa, and P. Braunstein (1986),J. Chem. Soc. Dalton Trans. 1135.
M. Castiglioni, R. Giordano, E. Sappa, A. Tiripicchio, and M> Tiripicchio Camellini (1986).J. Chem. Soc. Dalton Trans. 23.
M. Castiglioni, R. Giordano, and E. Sappa (1987).J. Organomet. Chem. 319, 167.
M. Castiglioni, R. Giordano, and E. Sappa (1988).J. Organomet. Chem. 342, 111.
See, for example: G. Süss-Fink and G. Herrmann (1985).J. Chem. Soc. Chem. Commun. 735.
Examples of cluster analysis are in: (a) F. A. Cotton and G. Wilkinson,Advanced Inorganic Chemistry, Vth Ed. (J. Wiley, New York, 1988), p. 1269; A detailed discussion of cluster analysis, considering the main classes of homogeneous reactions is in: (b) W. L. Gladfelter and K. J. Roesselet,in D. F. Shriver, H. D. Kaesz, and R. D. Adams (eds.),The Chemistry of Metal Cluster Complexes, Ch. 7 (VCH, New York, 1990), p.329; (c) G. Süss-Funk and G. Meister (1993).Adv. Organomet. Chem. 35, 41.
See for example: (a) D. Nucciarone, S. A. MacLaughlin, A. J. Carty, and S. Colbran (1989).Inorg. Synth. 26, 264, and references therein; (b) R. Bender, P. Braunstein, B. Metz, and P. Lemoine (1984).Organometallics,3, 381, and references therein; (c) G. Huttner and K. Knoll (1987).Angew. Chem. Int. Ed. Engl. 26, 743.
M. Castiglioni, R. Giordano, and E. Sappa (1989).J. Organomet. Chem. 362, 399.
M. Castiglioni, R. Giordano, and E. Sappa (1989).J. Organomet. Chem. 369, 419.
M. Castiglioni, R. Giordano, and E. Sappa (1991).J. Organomet. Chem. 407, 377.
S. A. MacLaughlin, N. J. Taylor, A. J. Carty (1982).Can. J. Chem. 60, 87.
R. Giordano, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, M. J. Mays, and M. P. Brown (1989).Polyhedron 8, 1855.
E. Sappa, P. Braunstein, A. Tiripicchio, H. Vahrenkamp, in preparation.
J. Lunniss, S. A. MacLaughlin, N. J. Taylor, A. J. Carty, and E. Sappa (1985),Organometallics,4, 2066.
See for examples: (a) K. Knoll, T. Fässler, and G. Huttner (1987).J. Organomet. Chem. 332, 309; (b) D. Buchholz, G. Huttner, and L. Zsolnai (1990).J. Organomet. Chem. 381, 97, and references therein; See also Ref. 160c.
F. Van Gastel, A. J. Carty, M. A. Pellinghelli, A. Tiripicchio, and E. Sappa (1990).J. Organomet. Chem. 385, C 50.
R. P. Rosen, G. L. Geoffroy, C. Bueno, M. R. Churchill, and R. B. Ortega (1983).J. Organomet. Chem. 254, 89.
M. Lanfranchi, A. Tiripicchio, A. J. Carty, and E. Sappa (1986).J. Chem. Soc. Dalton Trans. 2737.
F. Van Gastel, S. A. MacLaughlin, M. Lynch, A. J. Carty, E. Sappa, A. Tiripicchio, and M. Tiripicchio Camellini (1987).J. Organomet. Chem. 326, C 65.
D. Belletti, A. Tiripicchio, M. Tiripicchio Camellini, and E. Sappa (1990).J. Chem. Soc. Dalton Trans. 703.
(a) D. B. W. Yawney and F. G. A. Stone (1969).J. Chem. Soc. (A) 502; (b) G. L. Geoffroy and W. L. Gladfelter (1977).J. Am. Chem. Soc. 99, 7565; (c) T. Venäläinen and T. A. Pakkanen (1986).J. Organomet. Chem. 316, 183.
J. R. Fox, W. L. Gladfelter, G. L. Geoffroy, I. Tavanaiepour, S. Abdel-Mequid, and V. W. Day (1981).Inorg. Chem. 20, 3230; (b) J. Wang, M. Sabat, L. J. Lyons, and D. F. Shriver (1991).Inorg. Chem. 30, 382; See also Refs. 15, 41, and 56.
S. Aime, R. Gobetto, L. Milone, D. Osella, L. Violano, A. J. Arce, and Y. De Sanctis (1991).Organometallics 10, 2854.
R. D. Adams, Z. Li, P. Swepston, W. Wu, and J. Yamamoto (1992).J. Am. Chem. Soc. 114, 10657.
The formation of this type of complexes upon dehydrogenation of linear and cyclic dienes was first reported by: (a) A. J. P. Domingos, B. F. G. Johnson, and J. Lewis (1972).J. Organomet. Chem. 36, C 43; Similar complexes were found by: (b) S. Aime, L. Milone, D. Osella, G. A. Vaglio, M. Valle, A. Tiripicchio, and M. Tiripicchio Camellini (1979).Inorg. Chim. Acta 34, 49; Structural characterization and discussion for the osmium homologues are in: (c) A. J. Deeming and M. Underhill (1974).J. Chem. Soc. Dalton Trans. 1415; (d) R. J. Goudsmit, B. F. G. Johnson, J. Lewis, P. R. Raithy, and M. Rosales (1983).J. Chem. Soc. Dalton Trans. 2257; (e) A. J. Deeming (1986).Adv. Organomet. Chem. 26, 1.
(a) B. F. G. Johnson, J. Lewis, M. Martinelli, A. H. Wright, D. Braga, and F. Grepioni (1990).J. Chem. Soc. Chem. Commun. 364; (b) D. Braga, F. Grepioni, B. F. G. Johnson, J. Lewis, C. E. Housecroft, and M. Martinelli (1991).Organometallics 10, 1260.
M. Bianchi, G. Menchi, U. Matteoli, and F. Piacenti (1993).J. Organomet. Chem. 451, 139.
J. Evans and G. S. McNulty (1981).J. Chem. Soc. Dalton Trans. 2017.
N. Lugan, F. Laurent, G. Lavigne, T. P. Newcomb, E. W. Liimatta, and J.-J. Bonnet (1990)J. Am. Chem. Soc. 112, 8607.
J. A. Cabeza, J. M. Fernandez-Colinas, A. Llamazares, and V. Riera (1992).J. Mol. Catal. 71, L 7; (b) J. M. Cabezza, J. M. Fernandez-Colinas, A. Llamazares, and V. Riera (1992).Organometallics 11, 4355.
See for example: (a) B. C. Gates, L. Guezi, and H. Knoözinger (eds.),Metal Clusters in Catalysis (Elsevier, Amsterdam, 1986); (b) P. Braunstein and J. Rosé,in I. Bernal (ed.),Stereo Chemistry of Organometallic and Inorganic Compounds, Vol. 3 (Elsevier, Amsterdam, 1989); (c) J. P. Fackler, Jr. (ed.),Metal-Metal Bonds and Clusters in Chemistry and Catalysis (Plenum, New York, 1990).
M. Castiglioni, R. Giordano, E. Sappa, G. Predieri, and A. Tiripicchio (1984).J. Organomet. Chem. 270, C 7; (b) M. Castiglioni, R. Giordano, E. Sappa, and P. Volpe (1985).J. Chromatog. 349, 173.
M. Castiglioni, R. Giordano, and E. Sappa (1986).J. Mol. Catal. 37, 287; (b) F. Castagno, M. Castiglioni, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, P. Braunstein, and J. Rosé (1989).J. Chem. Soc. Dalton Trans. 1477; (c) M. Castiglioni, R. Giordano, and E. Sappa (1987).J. Mol. Catal. 40, L 65; (d) M. Castiglioni, R. Giordano, E. Sappa, E. Guglielminotti, G. Albanesi, P. Moggi, and G. Predieri,in R. M. Laine (ed.),Transformation of Organometallics into Common and Exotic Materials: Design and Activation (NATO ASI Series, n. 141, Martinus Nijhoff, Dordrecht, 1988), p. 56; See also Ref. 154.
P. Moggi, G. Albanesi, G. Predieri, and E. Sappa (1983).J. Organomet. Chem. 252, C 89; (b) G. Albanesi, R. Bernardi, P. Moggi, G. Predieri, and E. Sappa (1986).Gazz. Chim. Ital. 116, 385; (c) P. Moggi, G. Predieri, G. Albanesi, S. Papadopoulos, and E. Sappa (1989).Appl. Cat. 53, L1; (d) G. Predieri, P. Moggi, S. Papadopoulos, A. Armigliato, S. Bigi, and E. Sappa (1990).J. Chem. Soc. Chem. Commun. 1736; (b) A. Armigliato, S. Bigi, P. Moggi, S. Papadopoulos, G. Predieri, G. Salviati, and E. Sappa (1991).Mater. Chem. Phys. 29, 251.
M. Castiglioni, R. Giordano, E. Sappa, P. Baistrocchi, P. Moggi, and G. Predieri, XXII Congresso Naz. di Chimica Inorganica, Villasimius (Cagliari), Sept. 26–Oct. 1st (1993), Paper CO-06.
S. Aime and L. Gambino, L. Milone, E. Sappa, and E. Rosenberg (1975).Inorg. Chim. Acta 15, 53.
See for example: (a) S. Aime, L. Milone, and E. Sappa (1976).Inorg. Chim. Acta 16, L-7; (b) S. Aime, L. Milone, and E. Sappa (1976).J. Chem. Soc. Dalton Trans. 838.
S. Aime (1982).Inorg. Chim. Acta 62, 51.
S. Aime, L. Milone, D. Osella, and E. Sappa (1978).Inorg. Chim. Acta 29, L-211.
E. Rosenberg, E. V. Anslyn, C. Barner-Thorsen, S. Aime, D. Osella, R. Gobetto, and L. Milone (1984).Organometallics 3, 1790.
J. Bracker-Novak, S. Hajela, M. Lord, M. Zhang, E. Rosenberg, R. Gobetto, L. Milone, and D. Osella, (1990).Organometallics 9, 1379.
S. Aime, R. Bertoncello, V. Busetti, R. Gobetto, G. Granozzi, and D. Osella (1986).Inorg. Chem. 25, 4004.
E. Rosenberg, J. Bracker-Novak, S. Aime, R. Gobetto, and D. Osella (1989).J. Organomet. Chem. 365, 163.
S. Aime, R. Gobetto, D. Osella, L. Milone, and E. Rosenberg (1982).Organometallics 1, 640.
S. Aime, D. Osella, and G. E. Hawkes,in M. Gielen (ed.),Topics in Physical Organometallic Chemistry, Vol. 2, Ch. 3 (Freund Publishing House, London, 1989). p. 91, and references therein
S. Aime, L. Milone, D. Osella, G. E. Hawkes E. W. Randall (1979).J. Organomet. Chem. 178, 171.
S. Aime, D. Osella, L. Milone, G. E. Hawkes, and E. W. Randall (1981).J. Am. Chem. Soc. 103, 5920.
(a) S. Aime, R. Gobetto, D. Osella, G. E. Hawkes, and E. W. Randall (1984).J. Chem. Soc. Dalton Trans. 1863; (b) S. Aime, M. Botta, R. Gobetto, and D. Osella (1988).J. Chem. Soc. Dalton Trans. 791.
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Sappa, E. Reactions of ruthenium carbonyl clusters with alkynes. J Clust Sci 5, 211–263 (1994). https://doi.org/10.1007/BF01170711
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DOI: https://doi.org/10.1007/BF01170711