Lithiation selectivity in monoalkylamine/dialkylamine mixtures: A synthetic and ab initio molecular orbital study

Organometallics

Volumn 18, Issue 18, 1999, Pages 3589-3596

  Armstrong, David R ^a   Carstairs, Alexis ^a   Henderson, Kenneth W ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038625566     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990287c     Document Type: Article

References (90)

1. (a) Wakefield, B. J. Organolithium Methods; Academic Press: London, 1988.
2. (b) Heathcock, C. H. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: New York, 1980; Vol. B, Chapter 4.
3. (c) Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vols. 2 and 3.
4. (d) Snieckus, V. Chem. Rev. 1990, 90, 879.
5. (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
6. (b) Williard, P. G. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon: New York, 1991; Vol. 1, p 1.
7. (c) Klumpp, G. W. Recl. Trav. Chim. Pays-Bas. 1986, 105, 1.
8. (a) Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829.
9. (b) Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35.
10. (c) Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891.
11. (a) Frenna, V.; Vivona, N.; Consiglio, G.; Spinelli, D. J. Chem. Soc., Perkin Trans. 2 1985, 1865.
12. (b) Newcomb, M.; Burchill, M. T. J. Am. Chem. Soc. 1984, 106, 2450.
13. For reviews on kinetic asymmetric deprotonation by chiral lithium amides see: (a) Koga, K. J. Synth. Org. Chem. Jpn. 1990, 48, 463.
14. (b) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmerty 1991, 2, 1.
15. (c) Koga, K. Pure Appl. Chem. 1994, 66, 1487.
16. (d) Simpkins, N. S. Pure Appl. Chem. 1996, 68, 691.
17. (e) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439.
18. Armstrong, D. R.; Kennedy, A. R.; Mulvey, R. E.; Rowlings, R. B. Angew. Chem., Int. Ed. Engl. 1999, 38, 131.
19. Kocian, O.; Spencer, N.; Stoddart, J. F.; Cragg-Hine, I.; Davidson, M.; Mair, F. S.; Raithby, P.; Snaith, R.; Kottke, T.; Pohl, E. Tetrahedron 1995, 51, 579.
20. (a) Clegg, W.; Henderson, K. W.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. Chem. Eur. J. 1998, 4, 53.
21. (b) Beswick, M. A.; Choi, N.; Harmer, C. N.; McPartlin, M.; Mosquera, M. E. G.; Raithby, P. R.; Tombul, M.; Wright, D. S. Chem. Commun. 1998, 1383.
22. (c) Feeder, N.; Snaith, R.; Wheatley, A. E. H. Eur. J. Inorg. Chem. 1998, 879.
23. (d) Montero, M. L.; Wessel, H.; Roesky, H. W.; Teichert, M.; Uson, I. Angew. Chem., Int. Ed. Engl. 1997, 36, 629.
24. (a) Hascall, T.; Olmstead, M. M.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 1000.
25. (b) Hascall, T.; Ruhlandt-Senge, K.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1994, 33, 356.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
27. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
28. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
29. (c) Dill, J. D.; Pople, J. A. J. Chem. Phys. 1975, 62, 2921.
30. An excellent review of past and present theoretical studies of lithium compounds can be found in: Lithium Chemistry, A Theoretical and Experimental Overview; Sapse, A. M., Schleyer, P. v. R., Eds.; Wiley-Interscience: New York, 1995.
31. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
32. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
33. (a) Arnett, E. M. J. Chem. Educ. 1985, 62, 385.
34. (b) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; pp 296-316.
35. For data related to quantitative ion-pair acidity measurements using lithium amides see: (a) Furlong, J. J. P.; Lewkowicz, E. S.; Nudelman, N. S. J. Chem. Soc., Perkin Trans. 2 1990, 1461.
36. (b) Streitwieser, A., Jr.; Juaristi, E.; Nebenzahl, L. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevier: New York, 1980; Chapter 7.
37. (c) Fraser, R. R.; Baignee, A.; Bresse, M.; Hata, K. Tetrahedron Lett. 1982, 23, 4195.
38. (d) Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Chem. Soc., Chem. Commun. 1983, 620.
39. (e) Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Am. Chem. Soc. 1983, 105, 7790.
40. (f) Fraser, R. R.; Mansour, T. S.; Savard, S. J. Org. Chem. 1984, 49, 3442.
41. (g) Fraser, R. R.; Mansour, T. S. J. Am. Chem. Soc. 1984, 49, 3443.
42. (h) Fraser, R. R.; Mansour, T. S.; Savard, S. J. Org. Chem. 1985, 50, 3232.
43. (j) Fraser, R. R.; Mansour, T. S. Tetrahedron Lett. 1986, 27, 331.
44. Similarly, experimental gas-phase deprotonation enthalpies of amines are in the following order: secondary amines < primary amines < ammonia. See: Bartmess, J. E.; McIver, R. T., Jr. In Gas-Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Chapter 11, p 103.
45. (a) Brauman, J. I.; Blair, K. L. J. Am. Chem. Soc. 1968, 90, 6561.
46. (b) Brauman, J. I.; Blair, K. L. J. Am. Chem. Soc. 1970, 92, 5986.
47. (c) Baird, N. C. Can. J. Chem. 1969, 47, 2306.
48. (d) Lewis, T. P. Tetrahedron. 1969, 25, 4117.
49. (e) Huheey, J. E. J. Org. Chem. 1971, 36, 204.
50. For a discussion of negative hyperconjugation effects see: (a) Reed, A. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 1434.
51. (b) Schleyer, P. v. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467.
52. (c) Schleyer, P. v. R.; Kos, A. J. Tetrahedron 1983, 39, 1141.
53. (d) Bingham, R. C. J. Am. Chem. Soc. 1975, 97, 6743.
54. For a review of the basicity of amines see: Smith, J. W. In The Chemistry of the Amino Group; Patai, S., Ed.; Wiley: New York, 1968; p 161.
55. tBuH 448.1.
56. (a) Kremer, T.; Schleyer, P. v. R. Organometallics 1997, 16, 737.
57. (b) Abbotto, A.; Streitwieser, A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1997, 119, 11255.
58. (c) Schleyer, P. v. R.; Chandrasekhar, S.; Kos, A. J.; Clark, T.; Spitznagel, G. W. J. Chem. Soc., Chem. Commun. 1981, 882.
59. (a) Wurthwein, E.-U.; Sein, K. D.; Pople, J. A.; Schleyer, P. v. R. Inorg. Chem. 1983, 22, 496.
60. (b) Sapse, A. M.; Kaufman, E.; Schleyer, P. v. R.; Gleiter, R. Inorg. Chem. 1984, 23, 1569.
61. (c) Raghavachari, K. J. Chem. Phys. 1982, 76, 5421.
62. Calculations on monomers and dimers of simple lithium compounds have been carried out using a modified Born model to imitate solvent effects: Sapse, A. M.; Jain, D. C. J. Phys. Chem. 1987, 91, 3923.
63. Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707.
64. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217.
65. (a) Weiss, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 1501.
66. (b) Gregory, K. P.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47.
67. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167.
68. Williard, P. G.; Salvino, J. M. J. Org. Chem. 1993, 58, 1.
69. (a) Mulvey, R. E. Chem. Soc. Rev. 1998, 27, 339.
70. (b) Kennedy, A. R.; Mulvey, R. E.; Robertson, A. Chem. Commun. 1998, 89.
71. (c) Clegg, W.; Liddle, S. T.; Mulvey, R. E.; Robertson, A. Chem. Commun. 1999, 511.
72. (d) Barnett, N. D. R.; Clegg, W.; Horsburgh, L.; Lindsay, D. M.; Liu, Q.-Y.; Mackenzie, F. M.; Mulvey, R. E.; Williard, P. G. Chem. Commun. 1996, 2321.
73. (e) Barr, D.; Clegg, W.; Cowton, L.; Horsburgh, L.; Mackenzie, F. M.; Mulvey, R. E. J. Chem. Soc., Chem. Commun. 1995, 891.
74. Armstrong, D. R.; Barr, D.; Clegg, W.; Mulvey, R. E.; Reed, D.; Snaith, R.; Wade, K. J. Chem. Soc., Chem. Commun. 1986, 869.
75. 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.
76. For example, the structure of LDA is a helical polymer and LiTMP is an eight-membered ring tetramer: (a) Barnett, N. D. R.; Mulvey, R. E.; Clegg, W.; O'Neil, P. A. J. Am. Chem. Soc. 1991, 113, 8187.
77. (b) Lappert, M. F.; Slade, M. J.; Singh, A.; Atwood, J. L.; Rodgers, R. D.; Shakir, R. J. Am. Chem. Soc. 1983, 105, 302.
78. Henderson, K. W.; Williard, P. G. Unpublished results.
79. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 3529.
80. 2 oligomers: Raghavachari, K.; Sapse, A. M.; Jain, D. Inorg. Chem. 1987, 26, 2585.
81. Armstrong, D. R.; Barr, D.; Clegg, W.; Hodgson, S. M.; Mulvey, R. E.; Reed, D.; Snaith, R.; Wright, D. S. J. Am. Chem. Soc. 1989, 111, 4719.
82. 2 have been studied: Sorger, K.; Schleyer, P. v. R.; Fleischer, R.; Stalke, S. J. Am. Chem. Soc. 1996, 118, 6924.
83. (a) Dinnebier, R. E.; Behrens, U.; Olbrich, F. J. Am. Chem. Soc. 1998, 120, 1430.
84. (b) Eppinger, J.; Herdtweck, E.; Andwander, R. Polyhedron 1998, 17, 1195.
85. (c) Englich, U.; Chadwick, S.; Ruhlandt-Senge, K. Inorg. Chem. 1998, 37, 283.
86. (d) Smith, J. D. Angew. Chem., Int. Ed. Engl. 1998, 37, 2071.
87. (a) Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555.
88. (b) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349.
89. Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sentitive Compounds; John Wiley: New York, 1986.
90. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 4, 1879.