Solution structures of lithium monoalkylamides (RNHLi)

Organometallics

Volumn 18, Issue 16, 1999, Pages 2981-2987

  Aubrecht, Katherine B ^a   Lucht, Brett L ^a   Collum, David B ^a  

^a Department of Population Medicine and Diagnostic Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001539910     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om981051w     Document Type: Article

References (90)

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15. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829. Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35. For related dialkylamine-mediated aldol condensations see: Regan, A. C.; Staunton, J. J. Chem. Soc., Chem. Commun. 1983, 764. Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620.
16. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829. Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35. For related dialkylamine-mediated aldol condensations see: Regan, A. C.; Staunton, J. J. Chem. Soc., Chem. Commun. 1983, 764. Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620.
17. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829. Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35. For related dialkylamine-mediated aldol condensations see: Regan, A. C.; Staunton, J. J. Chem. Soc., Chem. Commun. 1983, 764. Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620.
18. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829. Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35. For related dialkylamine-mediated aldol condensations see: Regan, A. C.; Staunton, J. J. Chem. Soc., Chem. Commun. 1983, 764. Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 1620.
19. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
20. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
21. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
22. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
23. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
24. Hodgson, D. M.; Gibbs, A. R. Tetrahedron Lett. 1997, 38, 8907. Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567. Hodgson, D. M.; Gibbs, A. R. Tetrahedron: Asymmetry 1996, 7, 407. Koga, K. Pure Appl. Chem. 1994, 66, 1487. Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507. Milne, D.; Murphy, P. J. J. Chem. Soc., Chem. Commun. 1993, 884.
25. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891.
26. For other reactions of protic lithium amides see: Scollard, J. D.; McConville, D. H.; Vittal, J. J. Organometallics 1997, 16, 4415. Beswick, M. A.; Mosquera, M. E. G.; Wright, D. S. J. Chem. Soc., Dalton Trans. 1998, 2437.
27. For other reactions of protic lithium amides see: Scollard, J. D.; McConville, D. H.; Vittal, J. J. Organometallics 1997, 16, 4415. Beswick, M. A.; Mosquera, M. E. G.; Wright, D. S. J. Chem. Soc., Dalton Trans. 1998, 2437.
28. Wanat, R. A.; Collum, D. B.; Van Duyne, G.; Clardy, J.; DePue, R. T. J. Am. Chem. Soc. 1986, 108, 3415.
29. Lucht, B. L.; Collum, D. B J. Am. Chem. Soc. 1996, 118, 3529.
30. 2NLi structures see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Mulvey, R. E. Chem. Soc. Rev. 1998, 27. 339. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Collum, D. B. Acc. Chem. Res. 1993, 26, 227.
31. 2NLi structures see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Mulvey, R. E. Chem. Soc. Rev. 1998, 27. 339. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Collum, D. B. Acc. Chem. Res. 1993, 26, 227.
32. 2NLi structures see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Mulvey, R. E. Chem. Soc. Rev. 1998, 27. 339. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Collum, D. B. Acc. Chem. Res. 1993, 26, 227.
33. 2NLi structures see: Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47. Mulvey, R. E. Chem. Soc. Rev. 1998, 27. 339. Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167. Collum, D. B. Acc. Chem. Res. 1993, 26, 227.
34. 2NLi structures, see: Barr, D.; Clegg, W.; Hodgson, S. M.; Lamming, G, R.; Mulvey, R. E.; Scott, A. J.; Snaith, R.; Wright, D. S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1241. Lappert, M. F.; Slade, M. J.; Singh, A.; Atwood, J. L.; Rogers, R. D.; Shakir, R J. Am. Chem. Soc. 1983, 105, 302.
35. 2NLi structures, see: Barr, D.; Clegg, W.; Hodgson, S. M.; Lamming, G, R.; Mulvey, R. E.; Scott, A. J.; Snaith, R.; Wright, D. S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1241. Lappert, M. F.; Slade, M. J.; Singh, A.; Atwood, J. L.; Rogers, R. D.; Shakir, R J. Am. Chem. Soc. 1983, 105, 302.
36. Williard, P. G. Unpublished data.
37. Barnett, N. D. R.; Clegg, W.; Horsburgh, L.; Lindsay, D. M.; Liu, Q.-Y.; Mackenzie, F. M.; Mulvey, R. E.; Williard, P. G. J. Chem. Soc., Chem. Commun. 1996, 2321. Clegg, W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 2011. Also, see; Clegg, W.; Henderson, K. W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. Chem. Eur. J. 1998, 4, 53. Atwood, D. A.; Cowley, A. H.; Jones, R. A. Organometallics 1993, 12, 236.
38. Barnett, N. D. R.; Clegg, W.; Horsburgh, L.; Lindsay, D. M.; Liu, Q.-Y.; Mackenzie, F. M.; Mulvey, R. E.; Williard, P. G. J. Chem. Soc., Chem. Commun. 1996, 2321. Clegg, W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 2011. Also, see; Clegg, W.; Henderson, K. W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. Chem. Eur. J. 1998, 4, 53. Atwood, D. A.; Cowley, A. H.; Jones, R. A. Organometallics 1993, 12, 236.
39. Barnett, N. D. R.; Clegg, W.; Horsburgh, L.; Lindsay, D. M.; Liu, Q.-Y.; Mackenzie, F. M.; Mulvey, R. E.; Williard, P. G. J. Chem. Soc., Chem. Commun. 1996, 2321. Clegg, W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 2011. Also, see; Clegg, W.; Henderson, K. W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. Chem. Eur. J. 1998, 4, 53. Atwood, D. A.; Cowley, A. H.; Jones, R. A. Organometallics 1993, 12, 236.
40. Barnett, N. D. R.; Clegg, W.; Horsburgh, L.; Lindsay, D. M.; Liu, Q.-Y.; Mackenzie, F. M.; Mulvey, R. E.; Williard, P. G. J. Chem. Soc., Chem. Commun. 1996, 2321. Clegg, W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 2011. Also, see; Clegg, W.; Henderson, K. W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. Chem. Eur. J. 1998, 4, 53. Atwood, D. A.; Cowley, A. H.; Jones, R. A. Organometallics 1993, 12, 236.
41. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
42. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
43. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
44. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
45. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
46. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
47. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
48. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
49. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
50. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
51. Other structural motifs of lithium monoalkylamides have been found. (a) Nonprismatic higher oligomers: Kennedy, A. R.; Mulvey, R. E.; Robertson, A. J. Chem. Soc., Chem. Commun. 1998, 89. Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891. Kowach, G. R.; Warren, C. J.; Haushalter, R. C.; DiSalvo, F. J. Inorg. Chem. 1998, 37, 156. Clegg, W.; Horsburgh, L.; Dennison, P. R.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1996, 1065. Engelhardt, L. M.; Jacobsen, G. E.; Junk, P. C.; Raston, C. L.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1988, 1011. (b) Dimers: Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. C.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148. Kottke, T.; Klingebiel, V.; Noltemeyer, M.; Pieper, U.; Walter, S.; Stalke, D. Chem. Ber. 1991, 124, 1941. von Bülow, R.; Gornitzka, H.; Kottke, T.; Stalke, D. J. Chem Soc., Chem. Commun. 1996, 1639. Reed, D.; Barr, D.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Dalton Trans. 1986, 557. (c) Monomers: Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 822. Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur J. Inorg. Chem. 1998, 879.
52. For leading references to crystal structures of alkyllithiums and lithium alkoxides see: Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, p 1. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501. Beswick, M. A.; Wright, D. S. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 1, p 1.
53. For leading references to crystal structures of alkyllithiums and lithium alkoxides see: Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, p 1. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501. Beswick, M. A.; Wright, D. S. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 1, p 1.
54. For leading references to crystal structures of alkyllithiums and lithium alkoxides see: Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, p 1. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501. Beswick, M. A.; Wright, D. S. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 1, p 1.
55. For leading references to crystal structures of alkyllithiums and lithium alkoxides see: Williard, P. G. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 1, p 1. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353. Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501. Beswick, M. A.; Wright, D. S. In Comprehensive Organometallic Chemistry II; Pergamon: New York, 1995; Vol. 1, p 1.
56. 2/MeLi mixed aggregates see: Raghavachari, K.; Sapse, A.-M.; Jain, P. C. Inorg. Chem. 1987, 26, 2585. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, D. J. Am. Chem. Soc. 1996, 118, 6924.
57. 2/MeLi mixed aggregates see: Raghavachari, K.; Sapse, A.-M.; Jain, P. C. Inorg. Chem. 1987, 26, 2585. Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, D. J. Am. Chem. Soc. 1996, 118, 6924.
58. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217.
59. 15N coupling.
60. Several chiral 1,2-dialkyl-1,2-diamines were prepared. Their corresponding lithium amides displayed high pentane solubility, precluding the isolation of materials suitable for solution structural studies: Aubrecht, K. B. Ph.D. Dissertation, Cornell University, Ithaca, NY, 1999.
61. 2, first developed by J. H. Gilchrist, has been reported: Glueck, D. S.; Wu, J. X.; Hollander, F. J.; Bergman, K. G. J. Am. Chem. Soc, 1991, 113, 2041.
62. Gada, T.; Zwierzak, A. Synthesis 1981, 1005. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717.
63. Gada, T.; Zwierzak, A. Synthesis 1981, 1005. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717.
64. O'Brien, P.; Poumellec, P. Tetrahedron Lett. 1996, 37, 5619
65. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580. Also, see the Supporting Information in: Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 5810.
66. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580. Also, see the Supporting Information in: Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 5810.
67. Romesberg, F. E.; Bernstein, M. P.; Gilchrist, J. H.; Fuller, D. J.; Harrison, A. T.; Collum, D. B. J. Am. Chem. Soc. 1993, 115, 3475.
68. Günther, H. In Encyclopedia of Nuclear Magnetic Resonance; Wiley: Chichester, U.K., 1996; Vol. 5, p 2807.
69. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
70. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
71. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
72. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
73. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
74. Rapid intraaggregate exchange can cause coupling to all nuclei within the aggregate: Bauer, W. J. Am. Ckem. Soc. 1996, 118, 5450. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1986, 5, 1851. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255. Harder, S.; Ekhart, P. F.; Brandsma, L.; Kanters, J. A.; Duisenberg, A. J. M.; Schleyer, P. v. R. Organometallics 1992, 11, 2623. Bywater, S.; Lachance, P.; Worsfold, D. J. J. Phys. Chem. 1975, 79, 2148. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M J. J. Am. Chem. Soc. 1980, 102, 3345.
75. Intraaggregate exchange was observed in LiTMP: Hall, P. L.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9575.
76. 2NLi is observed in both the slow and fast exchange limits: Rutherford, J. L.; Collum, D. B. Unpublished data.
77. 15N coupling constants see: Koizumi, T.; Morihashi, K.; Kikuchi, O. Bull. Chem. Soc. Jpn. 1996, 69, 305.
78. The other methylene resonance is obscured.
79. Alternative exchange mechanisms involving N-Li bond scission are excluded because they would entail intraaggregate exchange, which is not observed.
80. Other doubly chelated lithium amide dimers have been observed: Reich, H. J.; Gudmundsson, B. O. J. Am. Chem. Soc. 1996, 118, 6074. Hilmersson, G.; Davidsson, O. J. Org. Chem. 1995, 60, 7660. Sato, D.; Kawasaki, H.; Shimada, L; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761.
81. Other doubly chelated lithium amide dimers have been observed: Reich, H. J.; Gudmundsson, B. O. J. Am. Chem. Soc. 1996, 118, 6074. Hilmersson, G.; Davidsson, O. J. Org. Chem. 1995, 60, 7660. Sato, D.; Kawasaki, H.; Shimada, L; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761.
82. Other doubly chelated lithium amide dimers have been observed: Reich, H. J.; Gudmundsson, B. O. J. Am. Chem. Soc. 1996, 118, 6074. Hilmersson, G.; Davidsson, O. J. Org. Chem. 1995, 60, 7660. Sato, D.; Kawasaki, H.; Shimada, L; Arata, Y.; Okamura, K.; Date, T.; Koga, K. J. Am. Chem. Soc. 1992, 114, 761.
83. For extensive leading references to the structures of lithium acetylides, see ref 37.
84. Thompson, A.; Corley, E. G.; Huntington, M. F.; Grabowski, E. J. J.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 2028.
85. 2NLi/RLi mixed aggregates see: Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Prigent, Y.; Davost, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175.
86. 2NLi/RLi mixed aggregates see: Corruble, A.; Valnot, J.-Y.; Maddaluno, J.; Prigent, Y.; Davost, D.; Duhamel, P. J. Am. Chem. Soc. 1997, 119, 10042. Hilmersson, G.; Davidsson, O. J. Organomet. Chem. 1995, 489, 175.
87. 2O. The major species has a prismatic structure.
88. Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1990, 112, 4069.
89. Cummins, C. C.; Wolezanski, P. T. Unpublished data.
90. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.