Intermetallic lithium-magnesium hexamethyldisilazide: Synthesis and structure, discovery of an oxygen-centered variant, and a reaction with benzonitrile that produces a novel amidinate cage compound with a trigonal bipyramidal Li4MgO core

Journal of the American Chemical Society

Volumn 120, Issue 31, 1998, Pages 7816-7824

  Kennedy, Alan R ^a   Mulvey, Robert E ^a   Rowlings, René B ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; LITHIUM DERIVATIVE; LITHIUM MAGNESIUM HEXAMETHYLDISILAZIDE; MAGNESIUM DERIVATIVE; METAL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032511369     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980561e     Document Type: Article

References (30)

1. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
2. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
3. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
4. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
5. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
6. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
7. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
8. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
9. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
10. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
11. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
12. For a selection of relevant papers from 1997 see: Williard, G.; Sun. C. J. Am. Chem. Soc. 1997, 119, 11693. (b) Hodgson, D. M.; Gibbs, R. Tetrahedron Lett. 1997, 38, 8907. (c) O'Brien, P.; Tournayre, J. J. Tetrahedron 1997, 53, 17527. (d) Blake, A. J.; Westaway, S. M.; Simpkins, N. S. Synlett 1997, 919. (e) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2283. (f) Yamashita, T.; Sato, D.; Kiyota, T,; Kumar, A.; Koga, K. Tetrahedron 1997, 53, 16987. (g) Tayebani, M.; Kasani, A.; Feghali, K.; Gambarotta, S.; Bensimon, C. J. Chem. Soc., Chem. Commun. 1997, 2001. (h) Fryzuk, M. D.; Hoffman, V.; Kickham, J. E.; Rettig, S. J.; Gambarotta, S. Inorg. Chem. 1997, 36, 3480. (i) Hwu, J. R.; Wong, F. F.; Huang, J. J.; Tsay, S. C. J. Org. Chem. 1997, 62, 4097. (j) Xun, X. F.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B.; J. Am. Chem. Soc. 1997, 119, 4765. (k) Legzdins, P.; Sayers, S. F. Chem. Eur. J. 1997, 3, 1579 (l) Corruble, A.; Valnot, J. Y.; Maddaluno, J.; Prigent, Y.; Davoust, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042.
13. For earlier reviews see (a) Williard, P. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1. (b) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. (c) Gregory, K.; Schleyer, P.v. R.; Snaith R. Adv. Inorg. Chem. 1991, 37, 47. (d) Pauer, F.; Power, P. P. In Lithium Chemistry: A Theoretical and Experimental Overview; Sapse, A.-M., Schleyer, P. v. R., Eds.; WileyInterscience: New York, 1995; Chapter 9.
14. For earlier reviews see (a) Williard, P. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1. (b) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. (c) Gregory, K.; Schleyer, P.v. R.; Snaith R. Adv. Inorg. Chem. 1991, 37, 47. (d) Pauer, F.; Power, P. P. In Lithium Chemistry: A Theoretical and Experimental Overview; Sapse, A.-M., Schleyer, P. v. R., Eds.; WileyInterscience: New York, 1995; Chapter 9.
15. For earlier reviews see (a) Williard, P. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 1, Chapter 1. (b) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. (c) Gregory, K.; Schleyer, P.v. R.; Snaith R. Adv. Inorg. Chem. 1991, 37, 47. (d) Pauer, F.; Power, P. P. In Lithium Chemistry: A Theoretical and Experimental Overview; Sapse, A.-M., Schleyer, P. v. R., Eds.; WileyInterscience: New York, 1995; Chapter 9.
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