Bis(2,4,6-tri-tert-butylphenyl)germylene reinvestigated: Crystal structure, Lewis acid catalyzed C-H insertion, and oxidation to an unstable germanone

Organometallics

Volumn 15, Issue 2, 1996, Pages 741-746

  Jutzi, Peter ^a   Schmidt, Holger ^a   Neumann, Beate ^a   Stammler, Hans Georg ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001324904     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950558t     Document Type: Article

References (67)

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33. 3 generally worked much slower: the fastest reaction was achieved in toluene, and there was found no difference between hexane and THF as a solvent.
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35. A similar deformation of a Mes* ligand has been found in several sterically overcrowded molecules: (a) Yoshifuji, M.;Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. Angew. Chem. 1980, 92, 405. (b) Yoshifuji, M.; Inamoto, N.; Hirotsu, K.; Higushi, T. J. Chem. Soc., Chem. Commun. 1985, 1109. (c) Weber, L.; Reizig, K.; Bungardt, D.; Boese, R. Chem. Ber. 1987, 120, 1421.
36. A similar deformation of a Mes* ligand has been found in several sterically overcrowded molecules: (a) Yoshifuji, M.;Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. Angew. Chem. 1980, 92, 405. (b) Yoshifuji, M.; Inamoto, N.; Hirotsu, K.; Higushi, T. J. Chem. Soc., Chem. Commun. 1985, 1109. (c) Weber, L.; Reizig, K.; Bungardt, D.; Boese, R. Chem. Ber. 1987, 120, 1421.
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44. 22
45. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
46. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
47. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
48. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
49. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
50. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
51. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
52. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
53. Stable adducts between germylenes and 16 valence-electron transition metal fragments have been isolated: (a) Marks, T. J. J. Am. Chem. Soc. 1971, 93, 7090. (b) Marks, T. C.; Newman, A. R. J. Am. Chem. Soc. 1973, 95, 769. (c) Jutzi, P.; Steiner, W. Chem. Ber. 1976, 109, 3473. (d) Jutzi, P.; Steiner, W. Angew. Chem. 1977, 89, 675. (e) Lappert, M. F., Miles, S. J.; Power, P. P.; Carty, A. J.; Taylor, N. J. J. Chem. Soc., Chem. Commun. 1977, 458. (f) Jutzi, P.; Steiner, W.; König, E.; Huttner, G.; Frank, A.; Schubert, U. Chem. Ber. 1978, 111, 606. (g) du Mont, W.-W.; Lange, L.; Pohl, S.; Saak, W. Organometallics 1990, 9, 1395. (h) Veith, M.; Becker, S.; Huch, V. Angew. Chem. 1990, 102, 186. (i) See ref 18.
54. The C-H insertion of a cationic center has been observed in some decomposition reactions: (a) Barclay, L. R. C.; MacDonald, M. C. Tetrahedron Lett. 1968, 7, 881. (b) Barclay, L. R. C.; Sonawane, H. R.; MacDonald, M. C. Can. J. Chem. 1972, 50, 281. (c) Cowley, A. H.; Kilduff, J. E.; Norman, N. C., Pakulski, M. J. Am. Chem. Soc. 1983, 105, 4845. (d) Okazaki, R.; Ishida, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1988, 40.
55. The C-H insertion of a cationic center has been observed in some decomposition reactions: (a) Barclay, L. R. C.; MacDonald, M. C. Tetrahedron Lett. 1968, 7, 881. (b) Barclay, L. R. C.; Sonawane, H. R.; MacDonald, M. C. Can. J. Chem. 1972, 50, 281. (c) Cowley, A. H.; Kilduff, J. E.; Norman, N. C., Pakulski, M. J. Am. Chem. Soc. 1983, 105, 4845. (d) Okazaki, R.; Ishida, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1988, 40.
56. The C-H insertion of a cationic center has been observed in some decomposition reactions: (a) Barclay, L. R. C.; MacDonald, M. C. Tetrahedron Lett. 1968, 7, 881. (b) Barclay, L. R. C.; Sonawane, H. R.; MacDonald, M. C. Can. J. Chem. 1972, 50, 281. (c) Cowley, A. H.; Kilduff, J. E.; Norman, N. C., Pakulski, M. J. Am. Chem. Soc. 1983, 105, 4845. (d) Okazaki, R.; Ishida, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1988, 40.
57. The C-H insertion of a cationic center has been observed in some decomposition reactions: (a) Barclay, L. R. C.; MacDonald, M. C. Tetrahedron Lett. 1968, 7, 881. (b) Barclay, L. R. C.; Sonawane, H. R.; MacDonald, M. C. Can. J. Chem. 1972, 50, 281. (c) Cowley, A. H.; Kilduff, J. E.; Norman, N. C., Pakulski, M. J. Am. Chem. Soc. 1983, 105, 4845. (d) Okazaki, R.; Ishida, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1988, 40.
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