Iron-carbene bonded to a planar tetraoxo surface defined by dimethoxy-p-tert-butylcalix[4]arene dianion

Organometallics

Volumn 16, Issue 26, 1997, Pages 5610-5612

  Giusti, Manuel ^a   Solari, Euro ^a   Giannini, Luca ^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

EID: 0001095759     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970751i     Document Type: Article

References (44)

1. Silver, J. Chemistry of Iron; Blackie: Glasgow, U.K., 1993. Pearson, A. J. Iron Compounds in Organic Synthesis; Academic: New York, 1994. Whitmire, K. H.; Kerber, R. C.; Fagan, P. J.; Akita, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 7; Chapters 1-4.
2. Silver, J. Chemistry of Iron; Blackie: Glasgow, U.K., 1993. Pearson, A. J. Iron Compounds in Organic Synthesis; Academic: New York, 1994. Whitmire, K. H.; Kerber, R. C.; Fagan, P. J.; Akita, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 7; Chapters 1-4.
3. Silver, J. Chemistry of Iron; Blackie: Glasgow, U.K., 1993. Pearson, A. J. Iron Compounds in Organic Synthesis; Academic: New York, 1994. Whitmire, K. H.; Kerber, R. C.; Fagan, P. J.; Akita, M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 7; Chapters 1-4.
4. Mechanisms of Reactions of Organometallic Compounds with Surfaces; Cole-Hamilton, D. J., Williams, J. O., Eds.; Plenum: New York, 1989. Cox, P. A. Transition Metal Oxides, an Introduction to their Electronic Structure and Properties; Oxford University Press: New York, 1992. Gates, B. A. Catalytic Chemistry; Wiley: New York, 1992.
5. Mechanisms of Reactions of Organometallic Compounds with Surfaces; Cole-Hamilton, D. J., Williams, J. O., Eds.; Plenum: New York, 1989. Cox, P. A. Transition Metal Oxides, an Introduction to their Electronic Structure and Properties; Oxford University Press: New York, 1992. Gates, B. A. Catalytic Chemistry; Wiley: New York, 1992.
6. Mechanisms of Reactions of Organometallic Compounds with Surfaces; Cole-Hamilton, D. J., Williams, J. O., Eds.; Plenum: New York, 1989. Cox, P. A. Transition Metal Oxides, an Introduction to their Electronic Structure and Properties; Oxford University Press: New York, 1992. Gates, B. A. Catalytic Chemistry; Wiley: New York, 1992.
7. Arduini, A.; Casnati, A. In Macrocycle Synthesis; Parker, O., Ed.; Oxford University Press: New York, 1996; Chapter 7.
8. A dimeric iron calix[4]arene where the metal is not available to any reactivity has been reported: Olmstead, M. M.; Sigel, G.; Hope, H.; Xu, X.; Power, P. P. J. Am. Chem. Soc. 1985, 107, 8087.
9. While homoleptic or monomeric alkoxo- or phenoxoiron(II) species are rare, a quite large number of iron aggregates containing alkoxo or phenoxo groups as coligands have been reported: (a) Komiya, S.; Tane-ichi, S.; Yamamoto, A.; Yamamoto, T. Bull. Chem. Soc. Jpn. 1980, 53, 673.
10. (b) Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
11. (c) Bartlett, R. A.; Ellison, J. J.; Power, P. P.; Shoner, S. C. Inorg. Chem. 1991, 30, 2888.
12. (d) Gupta, R.; Shah, A.; Singh, A.; Mehrotra, R. C. New J. Chem. 1991, 15, 665.
13. (e) Kato, M.; Yamada, Y.; Inagaki, T.; Mori, W.; Sakai, K.; Tsubomura, T.; Sato, M.; Yano, S. Inorg. Chem. 1995, 34, 2645.
14. (f) Caneschi, A.; Cornia, A.; Fabretti, A. C.; Gatteschi, D.; Malavasi, W. Inorg. Chem. 1995, 34, 4660.
15. (g) Caneschi, A.; Cornia, A.; Fabretti, A. C.; Foner, S.; Gatteschi, D.; Grandi, R.; Schenetti, L. Chem. Eur. J. 1996, 2, 1379 and references therein.
16. (h) Caneschi, A.; Cornia, A.; Lippard, S. J.; Papaefthymiou, G. C.; Sessoli, R. Inorg. Chim. Acta 1996, 243, 295.
17. Klose, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C.; Re, N. J. Am. Chem. Soc. 1994, 116, 9123.
18. For organometallic chemistry based on a calix[4]arene skeleton see: (a) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 753.
19. (b) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 85.
20. (c) Giannini, L.; Solari, E.; Zanotti-Gerosa, A.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2825.
21. (d) Castellano, B.; Zanotti-Gerosa, A.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1996, 15, 4894.
22. (e) Gardiner, M. G.; Lawrence, S. M.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1996, 2491.
23. (f) Gardiner, M. G.; Koutsantonis, G. A.; Lawrence, S. M.; Nichols, P. J.; Raston, C. L. Chem. Commun. 1996, 2035.
24. (g) Gibson, V. C.; Redshaw, C.; Clegg, W.; Elsegood, M. R. J. J. Chem. Soc., Chem. Commun. 1995, 2371.
25. (h) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542. 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.
26. (h) Acho, J. A.; Doerrer, L. H.; Lippard, S. J. Inorg. Chem. 1995, 34, 2542. 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.
27. B at 295 K. The solvation degree of the complexes was determined via both microanalysis and thermal decomposition, followed by a GC analysis.
28. For an iron(II) carbene functionality supported by a porphyrin ligand see: (a) Mansuy, D.; Lange, M.; Chottard, J. C.; Bartoli, J. F.; Chevrier, B.; Weiss, R. Angew. Chem. 1978, 90, 828.
29. (b) Mansuy, D. Pure Appl. Chem. 1980, 52, 681.
30. (c) Latos-Grazynski, L.; Cheng, R.-J.; La Mar, G. N.; Balch, A. L. J. Am. Chem. Soc. 1981, 103, 4270.
31. (d) Balch, A. L.; Cheng, R.-J.; La Mar, G. N.; Latos-Grazynski, L. Inorg. Chem. 1985, 24, 2651.
32. (e) Brothers, P. J.; Collman, J. P. Acc. Chem. Res. 1986, 19, 209.
33. (f) Mansuy, D. Pure Appl. Chem. 1987, 59, 759.
34. (g) Artaud, I.; Gregoire, N.; Battioni, J.-P.; Dupre, D.; Mansuy, D. J. Am. Chem. Soc. 1988, 110, 8714.
35. (h) Artaud, I.; Gregoire, N.; Leduc, P.; Mansuy, D. J. Am. Chem. Soc. 1990, 112, 6899.
36. Wolf, J. R.; Hamaker, C. G.; Djukic, J.-P.; Kodadek, T.; Woo, L. K. J. Am. Chem. Soc. 1995, 117, 9194.
37. (j) Ziegler, C. J.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5306.
38. (k) Mansuy, D.; Mahy, J. P. In Metalloporphyrin Catalyzed Oxidations; Montanari, F., Casella, L., Eds.; Kluwer: Dordrecht, The Netherlands, 1994; p 175.
39. 2 molecule of crystallization.
40. Crystallographic data are available in the Supporting Information.
41. -1, crystal dimensions 0.22 × 0.52 × 0.68 mm. The structure was solved by the heavy-atom method and anisotropically refined for all the non-H atoms except for the disordered atoms. For 3599 unique observed reflections (I > 2σ(I)) collected at T = 138 K on a Rigaku AFC6S diffractometer (5 < 2θ < 50°) and corrected for absorption the final conventional R is 0.075 (wR2 = 0.236 for the 6941 reflections having I > 0 used in the refinement). All calculations were carried out on a Quansan personal computer equipped with an Intel Pentium processor. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K. See the Supporting Information for more details.
42. (a) Riley, P. E.; Davis, R. E.; Allison, N. T.; Jones, W. M. Inorg. Chem. 1982, 21, 1321.
43. (b) Bauer, D.; Härter, P.; Herdtweck, E. J. Chem. Soc., Chem. Commun. 1991, 829.
44. The guest dichloromethane molecule was found to be statistically distributed over two positions (A and B), preventing the direct localization of the hydrogen atoms. The two nearly coplanar positions (dihedral angle 3.0(17)°) are oriented nearly parallel to the B and D rings (dihedral angles 21.3(12) [18.4(12)] and 21.5(12) [24.3(12)]°, respectively; values in brackets refer to molecule B) and perpendicular to the A and C rings (dihedral angles 87.9(8) [89.7(12)] and 88.0(10) [86.4(12)]°, respectively).