Bis(iminophosphorano)methane derivatives as precursors of unusual ruthenium carbene complexes: A synthetic and DFT study

Organometallics

Volumn 23, Issue 10, 2004, Pages 2421-2433

  Cadierno, Victorio ^a   Díez, Josefina ^a   García Álvarez, Joaquín ^a   Gimeno, José ^a   Calhorda, Maria José ^b,c   Veiros, Luis F ^d  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF LISBON   (Portugal)

^c INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^d INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CARBENE MOIETIES; DEPROTONATION; NUCLEOPHILES; PHOSPHORYLATION;

ORGANOMETALLICS;

EID: 2542496902     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030658w     Document Type: Article

References (136)

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30. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
31. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
32. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
33. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
34. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
35. 3 see: (a) Aguiar, A. M.; Aguiar, H. J.; Archibald, T. G. Tetrahedron Lett. 1966, 27, 3187. (b) Gilyarov, V. A.; Kovtun, V. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 5, 1159. (c) Kovtun, V. Y.; Gilyarov, V. A.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 11, 2612. (d) Appel, R.; Ruppert, I. Z. Anorg. Allg. Chem. 1974, 406, 131. (e) Imhoff, P.; Van Asselt, R.; Elsevier, C. J.; Vrieze, K.; Goubitz, K.; Van Malssen, K. F.; Stam, C. H. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 47, 401. (f) Al-Benna, S.; Sarsfield, M. J.; Thornton-Pett, M.; Ormsby, D. L.; Maddox, P. J.; Brès, P.; Bochmann, M. Dalton 2000, 4247.
36. 2} (Mes = 2,4,6-trimethylphenyl) is the only reported example of a bis(iminophosphorano) methane bearing dissimilar nitrogen-bound substituents: Hill, M. S.; Hitchcock, P. B. Dalton 2002, 4694.
37. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
38. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
39. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
40. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
41. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
42. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
43. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
44. See for example: (a) Balakrishna, M. S.; Santarsiero, B. D.; Cavell, R. G. Inorg. Chem. 1994, 33, 3079. (b) Reed, R. W.; Santarsiero, B.; Cavell, R. G. Inorg. Chem. 1996, 35, 4292. (c) Larré, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Eur. J. Inorg. Chem. 1999, 601. (d) Balakrishna, M. S.; Abhyankar, R. M.; Walawalker, M. G. Tetrahedron Lett. 2001, 42, 2733. (e) Alajarín, M.; López-Leonardo, C.; Llamas-Lorente, P. Tetrahedron Lett. 2001, 42, 605. (f) Balakrishna, M. S.; Teipel, S.; Pinkerton, A. A.; Cavell, R. G. Inorg. Chem. 2001, 40, 1802. (g) Longlet, J. J.; Bodige, S. G.; Watson, W. H.; Nielson, R. H. Inorg. Chem. 2002, 41, 6507. (h) Maraval, V.; Laurent, R.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. Synthesis 2003, 389.
45. (a) Kamalesh Babu, R. P.; Aparna, K.; McDonald, R.; Cavell, R. G. Inorg. Chem. 2000, 39, 4981.
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70. 1H} NMR signal was observed for the Ru=C carbon atoms, despite trials with long acquisition periods.
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