Complexes of transition metal carbonyls with alkynes. Closo- and nido-pentagonal bipyramidal clusters1

Journal of Organometallic Chemistry

Volumn 573, Issue 1-2, 1999, Pages 139-155

  Sappa, Enrico ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

, C5Me5, pentamethyl cyclopentadienyl; Alkynes; But, t butyl; Cp; Cp, C5H5, cyclopentadienyl; Isolobal relationships; Metal carbonyl clusters; Metallacyclic complexes; Organic syntheses

Indexed keywords

EID: 0000073472     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00706-2     Document Type: Article

References (145)

1. (a) W. Hubel, in: I. Wender, P. Pino (Eds), Organic Syntheses via Metal Carbonyls, vol. 1, Wiley-Interscience, New York, 1968, p. 273.
2. (b) E. Sappa, A. Tiripicchio, P. Braunstein, Chem. Rev. 83 (1983) 203.
3. (c) E. Sappa, J. Cluster Sci. 5 (1994) 211.
4. (a) N. Calderon, J.P. Lawrence, F.A. Ofstead, Adv. Organomet. Chem. 17 (1979) 449.
5. (b) R.R. Schrock, J. Organomet. Chem. 300 (1986) 249.
6. (c) N.E. Schore, Chem. Rev. 88 (1988) 1081.
7. (d) F. Biagini, A.M. Caporusso, T. Funaioli, C. Fachinetti, Angew. Chem. Int. Ed. Engl. 28 (1989) 1009.
8. (e) K.O. Bishop, Chem. Rev. 76 (1976) 461.
9. (f) R.J. Mc Kinney, J. Chem. Soc. Chem. Commun. (1980) 490.
10. (g) C. Otero Arean, E. Escalona Platero, G. Spoto, A. Zecchina, J. Mol. Catal. 56 (1989) 211.
11. Osella D., Dutto G., Nervi C., McGlinchey M.J., Vessieres A., Jaouen G. J. Organomet. Chem. 533:1997;97.
12. Bandy J.A., Bunting H.E., Garcia M.H., Green M.L.H., Marder S.R., Thompson M.E., Bloor D., Kolinsky P.V., Jones R.J., Perry J.W. Polyhedron. 11:1992;1429.
13. A discussion of clusters with alkynes coordinated in parallel or perpendicular fashion is in: S. Deabate, R. Giordano, E. Sappa, J. Cluster Sci. 8 (1997) 407.
14. Iron derivative: (a) R.P. Dodge, V. Shomaker, J. Organomet. Chem. 3 (1965) 274.
15. Ruthenium derivative: (b) S. Rivomanana, G. Lavigne, N. Lugan, J.-J. Bonnet, Organometallics 10 (1991) 2285.
16. Victor R., Usieli V., Sarel S. J. Organomet. Chem. 129:1977;387.
17. (a) E. Rosenberg, S. Aime, L. Milone, E. Sappa, A. Tiripicchio, A.M. Manotti Lanfredi, J. Chem. Soc. Dalton Trans. (1981) 2023.
18. (b) S.A.R. Knox, J. Cluster Sci. 3 (1992) 385.
19. Sappa E., Manotti Lanfredi A.M., Tiripicchio A. Inorg. Chim. Acta. 42:1980;255.
20. Sappa E., Predieri G., Tiripicchio A., Ugozzoli F. Gazz. Chim. Ital. 125:1995;51.
21. Gervasio G., Giordano R., Sappa E., Costa M., Predieri G., Tiripicchio A. J. Cluster Sci. 4:1993;33.
22. A.D. Shaposhnikova, G.L. Kamalov, R.A. Stadnichenko, A.A. Pasynskii, I.L. Eremenko, S.E. Nefedov, Yu. T. Struchov, A.I. Yanovsky, J. Organomet. Chem. 405 (1991) 111.
23. (a) O. Gambino, M. Valle, S. Aime, G.A. Vaglio, Inorg. Chim. Acta 8 (1974) 71.
24. (b) R.P. Ferrari, G.A. Vaglio, O.Gambino, M. Valle, G. Cetini, J. Chem. Soc. Dalton Trans. (1972) 1998.
25. (c) S. Aime, L. Milone, D. Osella, M. Valle, J. Chem. Res (S) (1978) 77; ibid (M) (1978) 785.
26. (c) S. Aime, L. Milone, D. Osella, M. Valle, J. Chem. Res (S) (1978) 77; ibid (M) (1978) 785.
27. Nuel D., Dahan F., Mathieu R. J. Am. Chem. Soc. 107:1985;1658.
28. (a) D. Lentz, H. Michael, Angew. Chem. Int. Ed. Engl. 28 (1989) 321.
29. (b) Idem, Chem. Ber. 121 (1988) 1413; J. Organomet. Chem. 327 (1989) 109.
30. (b) Idem, Chem. Ber. 121 (1988) 1413; J. Organomet. Chem. 327 (1989) 109.
31. (a) F. Van Gastel, A.J. Carty, M.A. Pellinghelli, A. Tiripicchio, E. Sappa, J. Organomet. Chem. 385 (1990) C50.
32. (b) J. Lunniss, S.A. MacLaughlin, N.J. Taylor, A.J. Carty, E. Sappa, Organometallics 4 (1985) 2066.
33. (c) J.F. Corrigan, S. Doherty, N.J. Taylor, A.J. Carty, Organometallics 12 (1993) 1365.
34. (d) K. Knoll, Th. Fassler, G. Huttner, J. Organomet. Chem. 332 (1987) 309.
35. (e) D. Buchholz, G. Huttner, L. Zsolnai, J. Organomet. Chem. 381 (1990) 97.
36. (a) M.L. Blohm, W.L. Gladfelter, Organometallics 5 (1986) 1049.
37. (b) J.S. Song, S.H. Han, N.T. Nguyen, G.L.Geoffroy, A.L. Rheingold, Organometallics 9 (1990) 2386.
38. (a) R.D. Adams, S. Wang, J. Am. Chem. Soc. 109 (1987) 924.
39. (b) R.D. Adams, J.E. Babin, M. Tasi, T.A. Wolf, Organometallics 6 (1987) 2228.
40. (c) Th. Fassler, G. Huttner, J. Organomet. Chem. 381 (1990) 391.
41. Eber B., Buchholz D., Huttner G., Fassler Th., Imhof W., Fritz M., Jochims J.C., Daran J.C., Jeannin J. J. Organomet. Chem. 401:1991;49.
42. Arce A.J., De Sanctis Y., Machado R., Capparelli M.V., Manzur J., Deeming A.J. Organometallics. 14:1995;3592.
43. (a) D. Osella, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, Inorg. Chim. Acta 42 (1980) 183.
44. (b) A. Tiripicchio, M. Tiripicchio Camellini, E. Sappa, J. Chem. Soc. Dalton Trans. (1984) 627.
45. Jaeger J.T., Powell A.K., Vahrenkamp H. Chem. Ber. 121:1988;1729.
46. First structural determinations on osmium derivatives (IA): G. Ferraris, G. Gervasio, J. Chem. Soc. Dalton Trans. (1972) 1057; (1973) 1933; (1974) 1813.
47. First structural determinations on osmium derivatives (IA): G. Ferraris, G. Gervasio, J. Chem. Soc. Dalton Trans. (1972) 1057; (1973) 1933; (1974) 1813.
48. First structural determinations on osmium derivatives (IA): G. Ferraris, G. Gervasio, J. Chem. Soc. Dalton Trans. (1972) 1057; (1973) 1933; (1974) 1813.
49. Complexes IB: A.A. Koridze, N.M. Astakhova, F.M. Dolgushin, A.I. Yanovsky, Yu. T. Struchov, P.V. Petrovskii, Organometallics 14 (1995) 2167.
50. K.J. Adams, J.J. Barker, S.A.R. Knox, A.G. Orpen, J. Chem. Soc. Dalton Trans. (1996) 975.
51. Kaesz H.D., King R.B., Manuel T.A., Nichols L.D., Stone F.G.A. J. Am. Chem. Soc. 82:1960;4749.
52. (a) G.N. Schrauzer, J. Am. Chem. Soc. 81 (1959) 5307.
53. (b) E.H. Braye, W. Hubel, J. Organomet. Chem. 3 (1965) 25.
54. (c) W. Hubel, E.H. Braye, J. Inorg. Nucl. Chem. 10 (1959) 250 {ibid. p. 204}.
55. (c) W. Hubel, E.H. Braye, J. Inorg. Nucl. Chem. 10 (1959) 250 {ibid. p. 204}.
56. See also: (d) G.E. Coates, M.L.H. Green, K.Wade, Organometallic Compounds, vol. II, Methuen, London, 1968, p. 303.
57. (a) H.W. Sternberg, R.A. Friedel, R.Markby, I. Wender, J. Am. Chem. Soc. 78 (1956) 3621.
58. (b) R. Clarkson, E.R.H. Jones, P.C. Wailes, M.C. Whiting, J. Am. Chem. Soc. 78 (1956) 6206. See also Ref. [26].
59. (a) A.A. Hock, O.S. Mills, Proc. Chem. Soc. (1958) 233.
60. (b) A.A. Hock, O.S. Mills, Acta Cryst. 14 (1961) 139.
61. S. Aime, L. Milone, E. Sappa, A. Tiripicchio, A.M. Manotti Lanfredi, J. Chem. Soc. Dalton Trans. (1979) 1664.
62. Rosenberger C., Steunou N., Jeannin S., Jeannin Y. J.Organomet.Chem. 494:1995;17.
63. P. Blenkiron, A.J. Carty, E. Sappa. (manuscript in preparation).
64. (a) P. Blenkiron, G.D. Enright, N.J. Taylor, A.J. Carty, Organometallics 15 (1996) 2855.
65. (b) P. Blenkiron, G.D. Enright, A.J. Carty, J. Chem. Soc. Chem. Commun. (1997) 483.
66. Milone L., Osella D., Ravera M., Stanghellini P.L., Stein E. Gazz. Chim. Ital. 122:1992;451.
67. Gervasio G., Sappa E. J. Organomet. Chem. 498:1995;73.
68. G. Gervasio, D. Marabello, E. Sappa, J. Chem. Soc. Dalton Trans. (1997) 1851.
69. Fassler T., Huttner G. J. Organomet. Chem. 376:1989;367.
70. Crocq V., Daran J.C., Jeannin Y. J. Organomet. Chem. 373:1989;85.
71. Imhof W. J. Organomet. Chem. 533:1997;31.
72. Han S.H., Geoffroy G.L., Rheingold A.L. Organometallics. 5:1986;2561.
73. Zimniak A., Zachara J. J. Organomet. Chem. 533:1997;45.
74. So far complexes I containing entirely metals not belonging to the iron triad have not been reported.
75. Moldes I., Papworth T., Ros J., Alvarez-Larena A., Piniella J.F. J. Organomet.Chem. 489:1995;65.
76. Predieri G., Tiripicchio A., Tiripicchio Camellini M., Costa M., Sappa E. J. Organomet. Chem. 423:1992;129.
77. Sunkel K. J. Organomet. Chem. 391:1990;247.
78. Hoffmann R. Angew. Chem. Int. Ed. Engl. 21:1982;711.
79. Hong F.-E., Lue I.-R., Lo S.-C., Lin C.-C. J. Organomet. Chem. 495:1995;97.
80. Chetcuti M.J., Grant B.E., Fanwick P.E. Organometallics. 14:1995;2937.
81. Connelly N.G., Escher T., Martin A.J., Metz B., Orpen A.G. J. Cluster Sci. 6:1995;125.
82. Cabrera E., Daran J.-C., Jeannin Y., Kristiansson O. J. Organomet. Chem. 310:1986;367.
83. Wade K. Adv. Inorg. Chem. Radiochem. 1:1976;18.
84. A concise but useful exposition on the relationships between boron hydrides, metal clusters is in: K.F. Purcell, J.C. Kotz, Inorganic Chemistry, Chapter 18, W.B. Saunders Company, Philadelphia, 1977, p. 980 and references therein.
85. A.A. Khoridze, A.M. Shaloumov, F.M. Dolgoushin, A.I. Ivanovskj, Yu. T. Struchov, P.V. Petrovskii, Russian Chem. Bull. 45 (1966) 702. See also Refs. [23,24].
86. Johnson B.F.G., Khattar R., Lewis J., Raithby P.R. J. Organomet. Chem. 335:1987;17.
87. (a) E. Sappa, A.M. Manotti Lanfredi, G. Predieri, A. Tiripicchio, A.J. Carty, J. Organomet. Chem. 288 (1985) 365.
88. (b) A. Sironi, G. Gervasio, E. Sappa, J. Cluster Sci. 5 (1994) 535. See also ref. ([1]c).
89. Scherer O.J., Berg G., Wolmershauser G. Chem. Ber. 128:1995;635.
90. Daran J.C., Gilbert E., Gouygou M., Halut S., Heim B., Jeannin Y. J. Cluster Sci. 5:1994;373.
91. Gunale A., Pritzkow H., Siebert W., Steiner D., Berndt A. Angew. Chem. Int. Ed. Engl. 34:1995;1111.
92. Osella D., Arman G., Gobetto R., Laschi F., Zanello P., Ayrton S., Goodfellow V., Housecroft C.E., Owen S.M. Organometallics. 8:1989;2689.
93. M. Casarin, D. Ajo, G. Granozzi, E. Tondello, S. Aime, Inorg. Chem. 24 (1985) 1241.
94. See also: (b) F.A. Cotton, Prog. Inorg. Chem. 21 (1976) 1.
95. (c) M. Bernard, A. Dedieu, S. Nakamura, New J. Chem. 8 (1984) 149.
96. Mealli C., Proserpio D.M. J. Chem. Educ. 67:1990;399.
97. E. Sappa. (unpublished results).
98. A.A. Koridze, A.I.Yanovski Yu., T. Struchov, J. Organomet. Chem. 441 (1992) 277.
99. In discussing the substitutional isomerism we take into account the more bulky substituants thus, an α-α-isomer is the one containing two bulky substituants on the C(σ) carbons of the ferrole ring (Fig. 1).
100. Bruce M.I., Zaitseva N.M., Skelton B.W., White A.H. Inorg.Chim. Acta. 250:1996;129.
101. J.P. Collman, L.S. Hegedus, Principles, Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley Cal, 1995, pp. 525-529 and references therein.
102. J.R. Berenguer, J. Fornies, E. Lalinde, F. Martinez, J. Chem. Soc. Chem. Commun. (1995) 1227.
103. Thorn D.L., Hoffmann R. Inorg. Chem. 17:1978;126.
104. Jeannin S., Jeannin Y., Robert F., Rosenberger C. J. Organomet. Chem. 480:1994;111.
105. W.P. Fehlhammer, M. Stolzenberg, in G. Wilkinson, F.G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry, 1st ed., vol. 4, Pergamon, Oxford, 1982, p. 548.
106. Cotton F.A., Troup J.M. J. Am. Chem. Soc. 96:1974;1233.
107. Dickson R.S. Polyhedron. 10:1991;1995.
108. Chetcuti M.J., Fanwick P.E., Gordon J.C. Inorg.Chem. 30:1991;4710.
109. (a) A. Mangia, G. Predieri, E. Sappa, Anal. Chim. Acta 152 (1983) 289.
110. (b) M. Careri, A. Mangia, P. Manini, G. Predieri, E. Sappa, J. Organomet. Chem. 476 (1994) 127.
111. Osella D., Gambino O., Nervi C., Ravera M. J. Organomet. Chem. 433:1992;287.
112. G. Gervasio, E. Sappa, L. Marko, J. Organomet. Chem. 444 (1993) 203. See also ref. [11].
113. Giordano R., Sappa E., Predieri G. Inorg. Chim. Acta. 228:1995;139.
114. L.A. Brady, A.F. Dyke, S.E. Garner, S.A.R. Knox, A. Irving, S.M. Nicholls, A.G. Orpen, J. Chem. Soc. Dalton Trans. (1993) 487.
115. E. Boroni, M. Costa, G. Predieri, E. Sappa, A. Tiripicchio, J. Chem. Soc. Dalton Trans. (1992) 2585.
116. (a) R.J.P. Corriu, J.J.E. Moreau, J. Chem. Soc. Chem. Commun. (1980) 278.
117. (b) F.A.Cotton, D.L.Hunter, J.M.Troup, Inorg.Chem., 15 (1976) 63.
118. D. Osella, M. Botta, R. Gobetto, R. Amadelli, V. Carassiti, J. Chem. Soc. Dalton Trans. (1988) 2519.
119. (a) E. Sappa, D. Cauzzi, G. Predieri, A. Tiripicchio, M. Tiripicchio Camellini, J. Organomet. Chem. 412 (1991) C14.
120. (b) R. Giordano, E. Sappa, D. Cauzzi, G. Predieri, M. Tiripicchio, J. Organomet. Chem. 511 (1996) 263. See also ref. 11.
121. (a) J. Piron, P. Piret, J. Meunier-Piret, M. van Meerssche, Bull. Soc. Chim. Belg. 78 (1969) 121.
122. (b) P. Piret, J. Meunier-Piret, M. van Meerssche, G.S.D. King, Acta Cryst. 19 (1965) 78.
123. Carre M.H., Moreau J.J.E. Inorg.Chem. 21:1982;3099.
124. Pettersen R.C., Cash C.G. Inorg. Chim. Acta. 34:1979;261.
125. Rivomanana S., Mongin C., Lavigne G. Organometallics. 15:1996;1195.
126. J.L. Davidson, M. Green, F.G.A. Stone, A.J. Welch, J. Chem. Soc. Dalton Trans. (1976) 2044.
127. Synthesis: (a) S. Aime, L. Milone, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, J. Chem. Soc. Dalton Trans. (1979) 1155, references therein. Structure: (b) A. Marzotto, M. Biagini Cingi, A. Ciccarese, D.A. Clemente, Acta Cryst. 96 (1991) C 47.
128. Synthesis: (a) S. Aime, L. Milone, E. Sappa, A. Tiripicchio, M. Tiripicchio Camellini, J. Chem. Soc. Dalton Trans. (1979) 1155, references therein. Structure: (b) A. Marzotto, M. Biagini Cingi, A. Ciccarese, D.A. Clemente, Acta Cryst. 96 (1991) C 47.
129. Knox S.A.R., Lloyd B.R., Morton D.A.V., Orpen A.G., Turner M.L., Hogarth G. Polyhedron. 14:1995;2723.
130. Blake A.J., Dyson P.J., Ingham S.L., Johnson B.F.G., Martin C.M. Organometallics. 14:1995;862.
131. Hirpo W., Curtis M.D., Kamp J.W. Organometallics. 11:1994;3360.
132. Cano A.C., Zuniga-Villareal N., Alvarez Toledano C., Toscano R.A., Cervantes M., Diaz A., Rudler H. J. Organomet. Chem. 464:1994;23.
133. Dickson R.S., Greaves B.C. Organometallics. 12:1993;3249.
134. R. Giordano, E. Sappa. (unpublished results).
135. Meunier-Piret J., Piret P., Van Meerssche M. Acta Cryst. 19:1965;85.
136. Sappa E., Milone L., Andreetti G.D. Inorg. Chim. Acta. 13:1975;67.
137. H. Adams, L.J. Gill, M.J. Morris, J. Chem. Soc. Dalton Trans. (1996) 3909.
138. Adams H., Gill L.J., Morris M.J. J. Organomet. Chem. 533:1997;117.
139. Giordano R., Sappa E. J. Organomet. Chem. 448:1993;157.
140. (a) D. Campagnola, M. Castiglioni, W. Dastru, S. Deabate, R. Giordano, P.J. King, E. Sappa, Inorg. Chim. Acta 262 (1997) 157.
141. (b) D. Campagnola, S. Deabate, R. Giordano, E. Sappa, J. Cluster Sci. 9 (1998) in press.
142. M. Castiglioni, R. Giordano, E. Sappa, J. Organomet. Chem. 407 (1991) 377 and references therein.
143. Giordano R., Sappa E., Knox S.A.R. J. Cluster Sci. 7:1996;179.
144. Gambino O., Sappa E., Cetini G. J. Organomet. Chem. 44:1972;185.
145. A discussion of these, other reactions involving cluster anions is in the forthcoming ESF book P. Braunstein, L. Oro, P.R. Raithby (Eds.), Metal Clusters in Chemistry, Wiley-VCH, New York.