-
2
-
-
0004085598
-
-
Langer, A. W., Jr., Ed.; American Chemical Society: Washington, D. C.
-
Polyamine-Chelated Alkali Metal Compounds; Langer, A. W., Jr., Ed.; American Chemical Society: Washington, D. C., 1974;
-
(1974)
Polyamine-Chelated Alkali Metal Compounds
-
-
-
3
-
-
0003613177
-
-
Hsieh, H. L., Quirk, R. P., Eds.; Marcel Dekker: New York
-
Anionic Polymerisation: Principles and Practical Applications', Hsieh, H. L., Quirk, R. P., Eds.; Marcel Dekker: New York, 1996:
-
(1996)
Anionic Polymerisation: Principles and Practical Applications'
-
-
-
6
-
-
2942585558
-
-
Mangelinckx, S.; Giubellina, N.; De Kimpe, N. Chem. Rev. 2004, 104, 2353:
-
(2004)
Chem. Rev.
, vol.104
, pp. 2353
-
-
Mangelinckx, S.1
Giubellina, N.2
De Kimpe, N.3
-
8
-
-
33746383574
-
-
U.S. Patent 3,451,988, 1960
-
The first report of a polyamine-modified organolithium reaction appeared in 1960: Langer, A. W., Jr. U.S. Patent 3,451,988, 1960.
-
-
-
Langer Jr., A.W.1
-
9
-
-
0003445429
-
-
Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg ; Chapter 26.2
-
Reviews describing some organolithium chemistry of imines: Denmark, S. E.; Nicaise. O. I.-C. In Comprehensive Asymmetric Catalvsis; Jacobsen, E. N., Pfaltz, A., Yamamoto, Y., Eds; Springer-Verlag: Heidelberg, 1999; Chapter 26.2;
-
(1999)
Comprehensive Asymmetric Catalvsis
-
-
Denmark, S.E.1
Nicaise, O.I.-C.2
-
12
-
-
0003417469
-
-
Trost, B. M., Fleming, I., Eds; Pergamon: Oxford : Chapter 1.12
-
Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: Oxford, 1991: Chapter 1.12;
-
(1991)
Comprehensive Organic Synthesis
-
-
Volkmann, R.A.1
-
16
-
-
0037116508
-
-
(b) Rutherford, J. L.; Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 2002, 124, 264.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 264
-
-
Rutherford, J.L.1
Hoffmann, D.2
Collum, D.B.3
-
17
-
-
0030857132
-
-
For spectroscopic studies confirming the structure of n-BuLi-TMEDA (7a), see: Waldmuller, D.; Kotsatos, B. J.; Nichols, M. A.; Williard, P. G. J. Am. Chem. Soc. 1997, 119, 5479;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 5479
-
-
Waldmuller, D.1
Kotsatos, B.J.2
Nichols, M.A.3
Williard, P.G.4
-
19
-
-
0003613693
-
-
Bach, R. O., Ed.; Wiley: New York
-
Fraenkel, G. In Lithium: Current Applications in Science, Medicine, and Technology; Bach, R. O., Ed.; Wiley: New York, 1985;
-
(1985)
Lithium: Current Applications in Science, Medicine, and Technology
-
-
Fraenkel, G.1
-
21
-
-
0000359986
-
-
Crassous, G.; Abadie, M.; Schue, F. Eur. Polym. J. 1979, 15, 747;
-
(1979)
Eur. Polym. J.
, vol.15
, pp. 747
-
-
Crassous, G.1
Abadie, M.2
Schue, F.3
-
22
-
-
0000930317
-
-
Also, see refs 6, 8, 11, and 17
-
Saà, J. M.; Martorell, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194; Also, see refs 6, 8, 11, and 17.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 5194
-
-
Saà, J.M.1
Martorell, G.2
Frontera, A.3
-
24
-
-
0001263348
-
-
(b) Barnett, N. D. R.; Mulvey, R. E.; Clegg, W.; O'Neil, P. A. J. Am. Chem. Soc. 1993, 115, 1573.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 1573
-
-
Barnett, N.D.R.1
Mulvey, R.E.2
Clegg, W.3
O'Neil, P.A.4
-
25
-
-
33748226760
-
-
(c) Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 580
-
-
Kottke, T.1
Stalke, D.2
-
26
-
-
0029798409
-
-
(a) Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 10707
-
-
Lucht, B.L.1
Bernstein, M.P.2
Remenar, J.F.3
Collum, D.B.4
-
27
-
-
0030861104
-
-
(b) Remenar, J. F.; Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1997, 119, 5567.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 5567
-
-
Remenar, J.F.1
Lucht, B.L.2
Collum, D.B.3
-
29
-
-
0001605768
-
-
Correlated solvation of lithium salts has been addressed computationally. For examples, see: Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometallics 1989, 8, 2577;
-
(1989)
Organometallics
, vol.8
, pp. 2577
-
-
Kaufmann, E.1
Gose, J.2
Schleyer, P.V.R.3
-
32
-
-
33746365531
-
-
Cheema, Z. W.; Gibson, G. W.; Eastham, J. F. J. Am. Chem. Soc. 1963, 85, 3517;
-
(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 3517
-
-
Cheema, Z.W.1
Gibson, G.W.2
Eastham, J.F.3
-
33
-
-
84916663446
-
-
Also, see ref 20
-
Denisov, V. M.; Melenevskaya, E. Yu.; Zgonnik, V. N.; Kol'tsov, A. I.; Sergutin, V. M. Izvestiva Akad. Nauk SSSR. Ser. Khim. 1976, 9, 1988; Also, see ref 20.
-
(1976)
Izvestiva Akad. Nauk SSSR. Ser. Khim.
, vol.9
, pp. 1988
-
-
Denisov, V.M.1
Melenevskaya, E.Yu.2
Zgonnik, V.N.3
Kol'tsov, A.I.4
Sergutin, V.M.5
-
36
-
-
0000255354
-
-
Abboud, J. L. M.; Yanez, M.; Elguero, J.; Liotard, D.; Essefar, M.; El Mouhtadi, M.; Taft, R. W. New J. Chem. 1992, 16, 739.
-
(1992)
New J. Chem.
, vol.16
, pp. 739
-
-
Abboud, J.L.M.1
Yanez, M.2
Elguero, J.3
Liotard, D.4
Essefar, M.5
El Mouhtadi, M.6
Taft, R.W.7
-
37
-
-
31444436125
-
-
For examples of diamine/dialkyl ether mixed-solvated alkyllithiums, see: Strohmann, C.; Daschlein, C.; Auer, D. J. Am. Chem. Soc. 2006, 128, 704;
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 704
-
-
Strohmann, C.1
Daschlein, C.2
Auer, D.3
-
38
-
-
0242490656
-
-
Strohmann, C.; Strohfeldt, K.; Schildbach, D. J. Am. Chem. Soc. 2003, 125, 13672;
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13672
-
-
Strohmann, C.1
Strohfeldt, K.2
Schildbach, D.3
-
39
-
-
0000661415
-
-
Buhl, M.; van Eikema Hommes, N. J. R.; Schleyer, P. v. R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459;
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 2459
-
-
Buhl, M.1
Van Eikema Hommes, N.J.R.2
Schleyer, P.V.R.3
Fleischer, U.4
Kutzelnigg, W.5
-
40
-
-
84985668655
-
-
Zarges, W.; Marsch, M.; Harms, K.; Boche, G. Chem. Ber. 1989, 122, 2303;
-
(1989)
Chem. Ber.
, vol.122
, pp. 2303
-
-
Zarges, W.1
Marsch, M.2
Harms, K.3
Boche, G.4
-
41
-
-
33748517465
-
-
Boche, G.; Marsch, M.; Muller, A.; Harms, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1032;
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 1032
-
-
Boche, G.1
Marsch, M.2
Muller, A.3
Harms, K.4
-
42
-
-
0342470648
-
-
Bräuer, M.; Weston, J.; Anders, E. J. Org. Chem. 2000, 65, 1193;
-
(2000)
J. Org. Chem.
, vol.65
, pp. 1193
-
-
Bräuer, M.1
Weston, J.2
Anders, E.3
-
43
-
-
0001648189
-
-
Gallagher, D. J.; Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1992, 114, 5872;
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5872
-
-
Gallagher, D.J.1
Kerrick, S.T.2
Beak, P.3
-
44
-
-
33748214773
-
-
Ledig, B.; Marsch, M.; Harms, K.; Boche, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 79.
-
(1992)
Angew. Chem., Int. Ed. Engl.
, vol.31
, pp. 79
-
-
Ledig, B.1
Marsch, M.2
Harms, K.3
Boche, G.4
-
45
-
-
0032578147
-
-
For related studies of phenyllithium in TMEDA/ethereal solvent mixtures, see: Reich, H. J.; Green, D. P.; Medina, M. A.; Goldenberg, W. S.; Gudmundsson, B. O.; Dykstra, R. R.; Phillips, N. H. J. Am. Chem. Soc. 1998, 120, 7201.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 7201
-
-
Reich, H.J.1
Green, D.P.2
Medina, M.A.3
Goldenberg, W.S.4
Gudmundsson, B.O.5
Dykstra, R.R.6
Phillips, N.H.7
-
46
-
-
84985059193
-
-
Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
-
(1983)
Helv. Chim. Acta
, vol.66
, pp. 308
-
-
Seebach, D.1
Hässig, R.2
Gabriel, J.3
-
47
-
-
0034537198
-
-
Rein, A. J.; Donahue, S. M.; Pavlosky, M. A. Curr. Opin. Drug Discov. Dev. 2000, 3, 734.
-
(2000)
Curr. Opin. Drug Discov. Dev.
, vol.3
, pp. 734
-
-
Rein, A.J.1
Donahue, S.M.2
Pavlosky, M.A.3
-
48
-
-
33748226760
-
-
n-BuLi was recrystallized from pentane: Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 580
-
-
Kottke, T.1
Stalke, D.2
-
49
-
-
0032875055
-
-
Equation Presented
-
6Li resonances (1:1) consistent with mixed dimer i, which is akin to that fully characterized previously: Arvidsson, P. I.; Hilmersson, G.; Davidsson, O. Chem. Eur. J. 1999, 5, 2348. (Equation Presented)
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 2348
-
-
Arvidsson, P.I.1
Hilmersson, G.2
Davidsson, O.3
-
50
-
-
33746330852
-
-
note
-
n-BuLi concentration refers to the total concentration (normality). TMCDA concentration refers to the concentration of the free (uncomplexed) ligand.
-
-
-
-
51
-
-
33746324350
-
-
note
-
The five-point curves in Figure 2 reveal inverse first orders, but with considerable error. The cited order of -1.0 derives from a more fully developed data set found in Supporting Information.
-
-
-
-
52
-
-
0034692916
-
-
Fukuda, T.; Takehara, A.; Hamiu, N.; Iwao, M. Tetrahedron: Asymmetry 2000, 11, 4083;
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 4083
-
-
Fukuda, T.1
Takehara, A.2
Hamiu, N.3
Iwao, M.4
-
53
-
-
0033607628
-
-
Also, see Yamada, H.; Kawate, T.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1999, 64, 8821.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 8821
-
-
Yamada, H.1
Kawate, T.2
Nishida, A.3
Nakagawa, M.4
-
54
-
-
30244499949
-
-
For the proper treatment of statistical factors, see: Benson, S. W. J. Am. Chem. Soc. 1958, 80, 5151;
-
(1958)
J. Am. Chem. Soc.
, vol.80
, pp. 5151
-
-
Benson, S.W.1
-
55
-
-
0000796832
-
-
For additional leading references to statistical contributions in "redistribution reactions," see: Fay, R. C.; Lowry, R. N. Inorg. Chem. 1974, 13, 1309.
-
(1974)
Inorg. Chem.
, vol.13
, pp. 1309
-
-
Fay, R.C.1
Lowry, R.N.2
-
56
-
-
33746330220
-
-
note
-
For studies of TMCDA-solvated lithium salts, see ref 9 and references therein.
-
-
-
-
57
-
-
1642415874
-
-
For leading references to high-coordinate lithium, see: Zhao, P.; Condo, A.; Keresztes, I.; Collum, D. B. J. Am. Chem. Soc. 2004, 126, 3113:
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3113
-
-
Zhao, P.1
Condo, A.2
Keresztes, I.3
Collum, D.B.4
-
58
-
-
33749831912
-
-
3 is a commonly observed octahedral coordination sphere: Bock, H.; Näther, C.; Havlas, Z.; John, A.; Arad, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 875.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 875
-
-
Bock, H.1
Näther, C.2
Havlas, Z.3
John, A.4
Arad, C.5
-
59
-
-
33746352170
-
-
note
-
We routinely find that calculated structures of congested systems backed with strong experimental support are challenging to minimize and often afford distortions (elongated bonds) that may or may not represent an adequate simulation.
-
-
-
-
60
-
-
33845379409
-
-
Open dimer-based mechanisms for 1,2-additions of alkyllithiums have been investigated computationally: (a) Kaufmann, E.; Schleyer, P. v. R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 5560
-
-
Kaufmann, E.1
Schleyer, P.V.R.2
Houk, K.N.3
Wu, Y.-D.4
-
61
-
-
0001273451
-
-
(b) Nakamura, E.; Nakamura, M.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 11016
-
-
Nakamura, E.1
Nakamura, M.2
Koga, N.3
Morokuma, K.4
-
63
-
-
0344443341
-
-
For additional leading references to spectroscopic, crystallographic, and kinetic evidence of open dimers, see: Zhao, P.; Collum, D. B. J. Am. Chem. Soc. 2003, 125, 14411:
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 14411
-
-
Zhao, P.1
Collum, D.B.2
-
64
-
-
0345240944
-
-
For calculations of monomer-based additions to a chiral hydrazone, see: Enders, D.; Diez, E.; Fernandez, R.; Martin-Zamora, E.; Munoz, J. M.; Pappalardo, R. R.; Lassaletta, J. M. J. Org. Chem. 1999, 64, 6329.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 6329
-
-
Enders, D.1
Diez, E.2
Fernandez, R.3
Martin-Zamora, E.4
Munoz, J.M.5
Pappalardo, R.R.6
Lassaletta, J.M.7
-
68
-
-
8844221234
-
-
Ramirez, A.; Candler, J.; Bashore, C. G.; Wirtz, M. C.; Coe, J. W.; Collum, D. B. J. Am. Chem. Soc. 2004, 126, 14700.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 14700
-
-
Ramirez, A.1
Candler, J.2
Bashore, C.G.3
Wirtz, M.C.4
Coe, J.W.5
Collum, D.B.6
-
69
-
-
0001542058
-
-
For an early report of a tetramer-based reaction requiring the dissociation of a coordinating ligand, see: Bartlett, P. D.; Goebel, C. V.; Weber, W. P. J. Am. Chem. Soc. 1969, 91, 7425.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 7425
-
-
Bartlett, P.D.1
Goebel, C.V.2
Weber, W.P.3
-
71
-
-
0035897440
-
-
For a structurally related triple ion bearing a TMEDA-chelated internal lithium, see: Bildmann, U. J.; Muller, G. Organometallics 2001, 20, 1689.
-
(2001)
Organometallics
, vol.20
, pp. 1689
-
-
Bildmann, U.J.1
Muller, G.2
-
72
-
-
0036284512
-
-
2 moiety. Differences between TMEDA and TMCDA as ligands have also been attributed to the fixed bite-angle of TMCDA: Heuger, G.; Kalsow, S.; Göttlich, R. Eur. J. Org. Chem. 2002, 1848.
-
(2002)
Eur. J. Org. Chem.
, pp. 1848
-
-
Heuger, G.1
Kalsow, S.2
Göttlich, R.3
-
73
-
-
33746338690
-
-
unpublished
-
We have found in a number of computational studies that ion pair separation in such destabilized lithium salts is inordinately costly. Ramirez A.; Collum, D. B., unpublished.
-
-
-
Ramirez, A.1
Collum, D.B.2
-
74
-
-
33746339320
-
-
note
-
5 Preliminary data using TMCDA appear to be consistent with an analogous scenario, but detailed rate studies were not completed.
-
-
-
-
75
-
-
0032554057
-
-
Rennels, R. A.; Maliakal, A.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 421.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 421
-
-
Rennels, R.A.1
Maliakal, A.2
Collum, D.B.3
-
77
-
-
0030910664
-
-
Sun, X.; Kenkre, S. L.; Remenar, J. F.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1997, 119, 4765.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4765
-
-
Sun, X.1
Kenkre, S.L.2
Remenar, J.F.3
Gilchrist, J.H.4
Collum, D.B.5
|