Ethylene rearrangement to M-C, M=C, and M=C functionalities over a tungsten-oxo surface illustrated by the W(IV) calix[4]arene fragment

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 823-824

  Giannini, Luca ^a   Solari, Euro ^a   Floriani, Carlo ^a   Chiesi Villa, Angiola ^b   Rizzoli, Corrado ^b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; ETHYLENE; TUNGSTEN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; SURFACE PROPERTY;

EID: 0032481359     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9734206     Document Type: Article

References (47)

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9. For related molecular approaches to oxo surfaces binding organometallic functionalities, see: Chisholm, M. H. Chemtracts:Inorg. Chem. 1992, 4, 273. Kläui, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 627. Feher, F. J.; Budzichowski, T. A. Polyhedron 1995, 14, 3239. Nagata, T.; Pohl, M.; Weiner, H.; Finke, R. G. Inorg. Chem. 1997, 36, 1366. Pohl, M.; Lyon, D. K.; Mizuno, N.; Nomiya, K.; Finke, R. G. Inorg. Chem. 1995, 34, 1413.
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12. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
13. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
14. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
15. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
16. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
17. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
18. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
19. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
20. For organometallic chemistry based on the calix[4]arene skeleton, see: (a) Giannini, L.; Caselli, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli C; Re, N.; Sgamellotti, A. J. Am. Chem. Soc. 1997, 119, 9198, 9709. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85. (d) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825. (e) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894. (f) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491. (g) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035. (h) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371. (i) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542.
21. cw = 31 Hz).
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26. 3).
27. t).
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33. Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1992, 11, 1771. Hill, J. E.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1991, 10, 3428. Takahashi, T.; Tamura, M.; Saburi, M.; Uchida, Y.; Negishi, E.-I. J. Chem. Soc., Chem. Commun. 1989, 852. Erker, G.; Czisch, P.; Krüger, C.; Wallis, J. M. Organometallics 1985, 4, 2059. Schrock, R. R.; McLain, S.; Sancho, J. Pure Appl. Chem. 1980, 52, 729. McLain, S.; Wood, C. D.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 4558.
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38. - reduction wave at about -1 V (-1.08 and -0.91 V, respectively).
39. 2}).
40. 2}).
41. Protonation and deprotonation of alkylidynes usually affects the coordination sphere of the metal. See: Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schrock, R. R.; Schubert, U.; Weiss, K. Carbyne Complexes; VCH: Weinheim, Germany, 1988; Chapter 5, p 189-190.
42. Van der Schaaf, P. A.; Hafner, A.; Mühlebach, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1845. Chamberlain, L. R.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Chem. Soc., Dalton Trans. 1987, 155. Chamberlain, L. R.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1987, 163. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847. Wood, C. D.; McLain, S. J.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 3210.
43. Van der Schaaf, P. A.; Hafner, A.; Mühlebach, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1845. Chamberlain, L. R.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Chem. Soc., Dalton Trans. 1987, 155. Chamberlain, L. R.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1987, 163. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847. Wood, C. D.; McLain, S. J.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 3210.
44. Van der Schaaf, P. A.; Hafner, A.; Mühlebach, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1845. Chamberlain, L. R.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Chem. Soc., Dalton Trans. 1987, 155. Chamberlain, L. R.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1987, 163. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847. Wood, C. D.; McLain, S. J.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 3210.
45. Van der Schaaf, P. A.; Hafner, A.; Mühlebach, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1845. Chamberlain, L. R.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Chem. Soc., Dalton Trans. 1987, 155. Chamberlain, L. R.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1987, 163. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847. Wood, C. D.; McLain, S. J.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 3210.
46. Van der Schaaf, P. A.; Hafner, A.; Mühlebach, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1845. Chamberlain, L. R.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Chem. Soc., Dalton Trans. 1987, 155. Chamberlain, L. R.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1987, 163. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847. Wood, C. D.; McLain, S. J.; Schrock, R. R. J. Am. Chem. Soc. 1979, 101, 3210.
47. -1: crystal dimensions 0.23 × 0.30 × 0.52 mm. For 5840 unique observed reflections [I > 2σ(I)] collected at T = 295 K on a Siemens SMART CCD (5° < 2θ < 46°) and corrected for absorption, the final R is 0.029 (wR2 = 0.069 for the 5870 reflections having I > 0 used in the refinement). For both 14 and 4 absorption correction was made according to: North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1968, A24, 351-359.