Reactivity of metallophosphide anions with electrophilic (arene)tricarbonylmetal complexes

European Journal of Inorganic Chemistry

Volumn , Issue 10, 2003, Pages 1893-1899

  Comte, Virginie ^a   Tranchier, Jean Philippe ^b   Rose Munch, Françoise ^b   Rose, Eric ^b   Perrey, Danièle ^a   Richard, Philippe ^a   Moïse, Claude ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b CNRS   (France)

Author keywords

Anions; Arene ligands; Carbonyl ligands; Chromium; Iron; Manganese

Indexed keywords

BINARY ALLOYS; CHROMIUM ALLOYS; CHROMIUM COMPOUNDS; FLUORINE COMPOUNDS; MANGANESE COMPOUNDS; NEGATIVE IONS;

ARENE CHROMIUM COMPLEX; ARENE LIGANDS; CARBONYL LIGAND; CATIONICS; CR COMPLEXES; DINUCLEAR COMPLEX; FLUORIDE ANIONS; MANGANESE COMPLEXES; METALLOPHOSPHIDE ANIONS; X-RAY STRUCTURE;

LIGANDS;

CHROMIUM DERIVATIVE; FLUORIDE; MANGANESE DERIVATIVE; METAL COMPLEX;

ARTICLE; CHEMICAL COMPOSITION; COMPARATIVE STUDY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0037533742     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200200531     Document Type: Article

References (50)

1. [1a] F. Mc Quillin, D. G. Parker, G. R. Stephenson, Transition Metal, Organometallics for Organic Synthesis, Cambridge University Press, Cambridge, 1991, p. 429.
2. [1b] M. F. Semmelhack, Comprehensive Organometallic Chemistry (Eds.: W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, vol. 12, chapter 9, p. 979.
3. [1c] K. F. McDaniel, Comprehensive Organometallic Chemistry (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, vol. 6, chapter 4, p. 93.
4. [1d] F. Rose-Munch, V. Gagliardini, C. Renard, E. Rose, Coord. Chem. Rev. 1998, 178-180, 249.
5. [1e] R. D. Pike, D. A. Sweigart, Coord. Chem. Rev. 1999, 187, 183.
6. [1f] D. Astruc, Chimie Organométallique, Ed. EDP Sciences, Les Ulis, France, 2000, p. 111.
7. [1g] F. Rose-Munch, E. Rose, Eur. J. Inorg. Chem. 2002, 6, 1269.
8. [1h] F. Rose-Munch, E. Rose, Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, chapter 11, p. 368.
9. [2a] A. R. Pape, K. P. Krishna, E. P. Kündig, Chem. Rev. 2000, 100, 2917.
10. [2bl G. Bernardinelli, S. Gillet, E. P. Kündig, L. Ronggang, A. Ripa, L. Saudan, Synthesis 2001, 13, 2040.
11. J. Breimair, M. Wieser, W. Beck, J. Organomet. Chem. 1992, 441, 429.
12. B. Niemer, J. Breimair, T. Völkel, B. Wagner, K. Polborn, W. Beck, Chem. Ber. 1991, 124, 2237.
13. B. Niemer, M. Steinmann, W. Beck, Chem. Res. 1988, 121, 1767.
14. J. Milke, K. Sünkel, W. Beck, J. Organomet. Chem. 1997, 543, 39.
15. X. Zhang, G. B. Carpenter, D. A. Sweigart, Organometallics 1999, 18, 4887.
16. H. Li, G. B. Carpenter, D. A. Sweigart, Organometallics 2000, 19, 1823.
17. [9a] For insertion of a Pd entity into the C-C1 bond of cationic Mn complexes, see: J. F. Carpentier, Y. Castanet, J. Brocard, A. Mortreux, F. Rose-Munch, C. Susanne, E. Rose, J. Organomet. Chem. 1995, 493, C22.
18. [9b] For insertion of a Pd entity into the C-Cl bond of Cr complexes, see for example: J. F. Carpentier, F. Petit, A. Mortreux, V. Dufaud, J. M. Basset, J. Thivolle-Cazat, J. Mol. Cat. 1993, 81, 1.
19. F. Rose-Munch, C. Susanne-Lecorre, F. Balssa, E. Rose, J. Vaissermann, E. Licandro, A. Papagni, S. Maiorana, W. Meng, R. Stephenson, J. Organomet. Chem. 1997, 545.
20. C. Renard, R. Valentic, F. Rose-Munch, E. Rose, J. Vaissermann, Organometallies 1998, 17, 1587.
21. [12a] J. A. Heppert, M. E. Thomas-Miller, P. N. Swepston, M. W. Extine, J. Chem. Soc., Chem. Commun. 1988, 280.
22. [12b] J. A. Heppert, M. E. Thomas-Miller, F. Takusagawa, M. A. Morgenstern, M. R. Shaker, Organometallics 1989, 8, 1199.
23. [12c] G. B. Richter-Addo, A. D. Hunter, N. Wichrowska, Can. J. Chem. 1990, 68, 41.
24. [13a] S. Rigny, J.-C. Leblanc, C. Moïse, New J. Chem. 1995, 19, 145.
25. [13b] S. Rigny, J.-C. Leblanc, C. Moïse, B. Nuber, New J Chem. 1997, 21, 469.
26. [13c] S. Rigny, V. I. Bakhmutov, B. Nuber, J.-C. Leblanc, C. Moïse, Inorg. Chem. 1996, 35, 3202.
27. [13d] V. Comte, O. Blacque, M. M. Kubicki, C. Moïse, Organometallics 2001, 20, 5432.
28. [14a] For the preparation of la see: A. M. Munro, P. L. Pauson, Z. Anorg. Allg. 1979, 458, 211.
29. [14b] For preparation of lb, see: P. L. Pauson, J. A. Segal, J. Chem. Soc. 1975, 1677.
30. [14c] For the preparation of 1c, see: F. Balssa, V. Gagliardini, F. Rose-Munch, E. Rose, Organometallics 1996, 15, 4373.
31. For the preparation of 4a, see: [15a] C. A. L. Mahaffy, J. Organomet. Chem. 1984, 262, 33. For the preparation of 4b and 4c, see: [15b] G. Winkhaus, L. Pratt, G. Wilkinson, J. Chem. Soc. 1961, 3807.
32. For the preparation of 4a, see: [15a] C. A. L. Mahaffy, J. Organomet. Chem. 1984, 262, 33. For the preparation of 4b and 4c, see: [15b] G. Winkhaus, L. Pratt, G. Wilkinson, J. Chem. Soc. 1961, 3807.
33. 2H was prepared by a published procedure: V. D. Bianco, S. Doronzo, Inorg. Synth. 1976, 16, 162.
34. + was already described: P. J. C. Walker, A. J. Mawby, Inorg. Chim. Acta 1973, 7, 621. However, the corresponding addition product was obtained in a very small amount which, according to the authors, rendered impossible complete characterisation of the complex which decomposed during attempted purification.
35. [18a] S. Rigny, Thesis, Université de Bourgogne, 1995.
36. [18b] We were unable to purify complexes 3c[Fe] and 6a[Fe] for stability reasons.
37. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
38. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
39. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
40. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
41. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
42. Such a regioselectivity has been observed for other nucleophiles adding meta to the MeO substituent of the arene ring, see for example: [19a] A. J. Pearson, I. C. Richards, J. Organomet. Chem. 1983, 258, C41. [19b] R. P. Alexander, G. R. Stephenson, J. Organomet. Chem. 1986, 314, C73. [19c] Y. K. Chung, H. K. Bae, I. N. Jung, Bull. Korean Chem. Soc. 1988, 9, 349. [19d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S. H. Lee, J. Chem. Soc., Chem. Commun. 1989, 659. [19e] W. H. Miles, P. M. Smiley, H. R. Brinkman, J. Chem. Soc., Chem. Commun. 1989, 1897. [19f] F. Balssa, V. Gagliardini, C. Lecorre-Susanne, F. Rose-Munch, E. Rose, J. Vaissermann, Bull. Soc. Chim. Fr. 1997, 134, 537.
43. Complex 5a has already been synthesised by treating the lithium derivative of (benzene)tricarbonylchromium complexes with chloro(diphenyl)phosphane: [20a] W. R. Cullen, S. J. Rettig, H. Zhang, Can. J. Chem. 1996, 74, 2167. Alternative: transmetallation of a stannous derivative of (benzene)tricarbonylchromium complexes with nBuLi followed by treatment with chloro-(diphenyl)phosphane: [20b] W. E. Wright, L. Lawson, B. T. Baker, D. C. Rae, Tetrahedron 1993, 11, 323.
44. Complex 5a has already been synthesised by treating the lithium derivative of (benzene)tricarbonylchromium complexes with chloro(diphenyl)phosphane: [20a] W. R. Cullen, S. J. Rettig, H. Zhang, Can. J. Chem. 1996, 74, 2167. Alternative: transmetallation of a stannous derivative of (benzene)tricarbonylchromium complexes with nBuLi followed by treatment with chloro-(diphenyl)phosphane: [20b] W. E. Wright, L. Lawson, B. T. Baker, D. C. Rae, Tetrahedron 1993, 11, 323.
45. V. Comte, C. Moïse, F. Rose-Munch, E. Rose, unpublished results.
46. F. Van Meurs, J. M. A. Baas, H. Van Bekkum, J. Organomet. Chem. 1976, 113, 353.
47. J. P. Djukic, F. Rose-Munch, E. Rose, J. Vaissermann, Eur. J. Inorg. Chem. 2000, 1295 and references therein.
48. M. J. Breen, P. M. Shulman, G. L. Geoffroy, A. L. Rheingold, W. C. Fultz, Organometallics 1984, 3, 782.
49. G. M. Sheldrick, SHELX97, Programs for Crystal Structure Analysis (includes SHELXS-97, SHELXL-97), release 97-2, University of Göttingen, Germany, 1998.
50. L. J. J. Farrugia, Appl. Crystallogr. 1999, 32, 837.