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1
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33845786925
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(a) Popowycz, F.; Routier, S.; Joseph, B.; Merour, J.-Y. Tetrahedron 2007, 63, 1031.
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2
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34447333366
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(b) Fang, Y.-Q.; Yuen, J.; Lautens, M. J. Org. Chem. 2007, 72, 5152.
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4
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34250678785
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(b) Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120.
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6
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0026571191
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Davis, M. L.; Wakefield, B. J.; Wardell, J. A. Tetrahedron 1992, 48, 939.
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Davis, M.L.1
Wakefield, B.J.2
Wardell, J.A.3
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9
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77957786498
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(a) Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, E. J. Adv. Heterocycl. Chem 1991, 52, 187.
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Quéguiner, G.1
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13
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22244435422
-
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Rappoport, Z, Marek, I, Eds, Wiley: New York
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(e) Clayden, J. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: New York, 2004; Vol. 1, p 495.
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(2004)
The Chemistry of Organolithium Compounds
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-
-
Clayden, J.1
-
19
-
-
85164042370
-
-
19F NMR spectroscopy, see: (a) Gakh, Y. G.; Gakh, A. A.; Gronenborn, A. M. Magn. Reson. Chem. 2000, 38, 551.
-
19F NMR spectroscopy, see: (a) Gakh, Y. G.; Gakh, A. A.; Gronenborn, A. M. Magn. Reson. Chem. 2000, 38, 551.
-
-
-
-
20
-
-
58049205784
-
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(b) McGill, C. A.; Nordon, A.; Littlejohn, D. J. Process Anal. Chem. 2001, 6, 36.
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(2001)
J. Process Anal. Chem
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, pp. 36
-
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McGill, C.A.1
Nordon, A.2
Littlejohn, D.3
-
21
-
-
58049214351
-
-
Scheme 2 does not represent a comprehensive profile of byproducts
-
Scheme 2 does not represent a comprehensive profile of byproducts.
-
-
-
-
24
-
-
0000815252
-
-
2 rearomatization, see: (a) Godard, A.; Jacquelin, J. M.; Quéguiner, G. J. Organomet. Chem. 1988, 354, 273.
-
2 rearomatization, see: (a) Godard, A.; Jacquelin, J. M.; Quéguiner, G. J. Organomet. Chem. 1988, 354, 273.
-
-
-
-
25
-
-
0029068299
-
-
(b) Eynde, J. J.; Delfosse, F.; Mayence, A.; Haverbeke, V. Tetrahedron 1995, 51, 6511.
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(1995)
Tetrahedron
, vol.51
, pp. 6511
-
-
Eynde, J.J.1
Delfosse, F.2
Mayence, A.3
Haverbeke, V.4
-
26
-
-
0022462472
-
-
For the 1,2-addition of an aryllithium to 1, see: DuPriest, M. T.; Schmidt, C. L.; Kuzmich, D.; Williams, S. B. J. Org. Chem. 1986, 51, 2021.
-
For the 1,2-addition of an aryllithium to 1, see: DuPriest, M. T.; Schmidt, C. L.; Kuzmich, D.; Williams, S. B. J. Org. Chem. 1986, 51, 2021.
-
-
-
-
27
-
-
58049191889
-
-
Dimer 9 was further characterized by X-ray crystallography. The product of oxidative coupling (i) was also characterized as a rogue crystal by X-ray crystallography. We were unable to intentionally produce detectable i by introducing oxygen to an LDA/1 mixture. (Chemical Equation Presented)
-
Dimer 9 was further characterized by X-ray crystallography. The product of oxidative coupling (i) was also characterized as a rogue crystal by X-ray crystallography. We were unable to intentionally produce detectable i by introducing oxygen to an LDA/1 mixture. (Chemical Equation Presented)
-
-
-
-
28
-
-
58049199618
-
-
We find fluoropyridines to be sensitive to traces of acid, including the residual HCl in chlorinated solvents
-
We find fluoropyridines to be sensitive to traces of acid, including the residual HCl in chlorinated solvents.
-
-
-
-
33
-
-
58049199620
-
-
Traces (approx 5, of 13(δ-77.9 ppm) are also observed
-
Traces (approx 5%) of 13(δ-77.9 ppm) are also observed.
-
-
-
-
34
-
-
58049212379
-
-
Lithiation of an isolated sample of 9 with LDA affords new 19 F resonances at δ-78.9 and-75.0 ppm that we attribute to ii. These resonances were not observed in the reaction mixture.
-
Lithiation of an isolated sample of 9 with LDA affords new 19 F resonances at δ-78.9 and-75.0 ppm that we attribute to ii. These resonances were not observed in the reaction mixture.
-
-
-
-
35
-
-
34250883890
-
-
For a review of rate studies of LDA-mediated reactions, see
-
For a review of rate studies of LDA-mediated reactions, see: Collum, D. B.; McNeil, A. J.; Ramirez, A. Angew. Chem., Int. Ed. 2007, 46, 3002.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 3002
-
-
Collum, D.B.1
McNeil, A.J.2
Ramirez, A.3
-
36
-
-
58049210873
-
-
We define the idealized rate law as that obtained by rounding the observed reaction orders to the nearest rational order
-
We define the idealized rate law as that obtained by rounding the observed reaction orders to the nearest rational order.
-
-
-
-
37
-
-
36749006077
-
-
and references cited therein
-
Ma, Y.; Collum, D. B. J. Am. Chem. Soc. 2007, 129, 14818, and references cited therein.
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(2007)
J. Am. Chem. Soc
, vol.129
, pp. 14818
-
-
Ma, Y.1
Collum, D.B.2
-
38
-
-
58049191888
-
-
For leading references and discussion of high-coordinate lithium amides, see ref 20
-
For leading references and discussion of high-coordinate lithium amides, see ref 20.
-
-
-
-
39
-
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33748493881
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(a) van Eikema Hommes, N. J. R.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1992, 31, 755.
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van Eikema Hommes, N.J.R.1
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84985688651
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(b) Stalke, D.; Klingebiel, U.; Sheldrick, G. M. Chem. Ber. 1988, 121, 1457.
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Stalke, D.1
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41
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0006011443
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(c) Armstrong, D. R.; Khandelwal, A. H.; Kerr, L. C.; Peasey, S.; Raithby, P. R.; Shields, G. P.; Snaith, R.; Wright, D. S. Chem. Commun. 1998, 1011.
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Armstrong, D.R.1
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Raithby, P.R.5
Shields, G.P.6
Snaith, R.7
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43
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0031437774
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(e) Henderson, K. W.; Dorigo, A. E.; Liu, Q.-Y.; Williard, P. G. J. Am. Chem. Soc. 1997, 119, 11855.
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Henderson, K.W.1
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44
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0034644389
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(f) Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640.
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Chadwick, S.T.1
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45
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33847612747
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(g) Chadwick, S. T.; Ramirez, A.; Gupta, L.; and Collum, D. B. J. Am. Chem. Soc. 2007, 129, 2259.
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Collum, D.B.4
-
48
-
-
58049208792
-
-
5 due to the especially large kinetic isotope effect on the metalation.
-
5 due to the especially large kinetic isotope effect on the metalation.
-
-
-
-
49
-
-
33748223894
-
-
It has been suggested that the n-BuLi adduct of pyridine can reduce pyridine by extruding lithium hydride, a Clegg, W, Dunbar, L, Horsburgh, L; Mulvey, R. E. Angew. Chem, Int. Ed. Engl. 1996, 35, 753
-
It has been suggested that the n-BuLi adduct of pyridine can reduce pyridine by extruding lithium hydride. (a) Clegg, W.; Dunbar, L.; Horsburgh, L; Mulvey, R. E. Angew. Chem., Int. Ed. Engl. 1996, 35, 753.
-
-
-
-
50
-
-
58049201184
-
-
obsdt) showed some discrepancies (Supporting Information), yet a fit to a nonlinear Noyes equation (ref 26b) to obtain the order by best-fit methods revealed an order of 1.0.
-
obsdt) showed some discrepancies (Supporting Information), yet a fit to a nonlinear Noyes equation (ref 26b) to obtain the order by best-fit methods revealed an order of 1.0.
-
-
-
-
51
-
-
33750439535
-
-
(b) Briggs, T. F.; Winemiller, M. D.; Collum, D. B.; Parsons, R. L., Jr.; Davulcu, A. K.; Harris, G. D.; Fortunak, J. D.; Confalone, P. N. J. Am. Chem. Soc. 2004, I26, 6291.
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Briggs, T.F.1
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Collum, D.B.3
Parsons Jr., R.L.4
Davulcu, A.K.5
Harris, G.D.6
Fortunak, J.D.7
Confalone, P.N.8
-
52
-
-
58049203362
-
-
obsd for the decay of 5 shows a minor (50%) rise with a 3-fold decrease in THF concentration.
-
obsd for the decay of 5 shows a minor (50%) rise with a 3-fold decrease in THF concentration.
-
-
-
-
53
-
-
58049197325
-
-
The crossover described in Scheme 3 occurs at substantially lower temperatures than the rearrangement to provide 10. As expected, analogous crossover is observed in 10.
-
The crossover described in Scheme 3 occurs at substantially lower temperatures than the rearrangement to provide 10. As expected, analogous crossover is observed in 10.
-
-
-
-
54
-
-
58049217940
-
-
We have never observed [6Li]LiF by NMR spectroscopy. This may derive from a very low solubility
-
6Li]LiF by NMR spectroscopy. This may derive from a very low solubility.
-
-
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55
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0034537198
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0001862940
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43249109110
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Crystal structures of amidinolithiums: Aharonovich, S.; Kapon, M.; Botoshanski, M.; Eisen, M. S. Organometallics 2008, 27, 1869.
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Crystal structures of amidinolithiums: Aharonovich, S.; Kapon, M.; Botoshanski, M.; Eisen, M. S. Organometallics 2008, 27, 1869.
-
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62
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33846661111
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-
For calculated open dimer-based additions of methyllithium to nitriles, see
-
For calculated open dimer-based additions of methyllithium to nitriles, see: Uchiyama, M.; Matsumoto, Y.; Usui, S.; Hashimoto, Y.; Morokuma, K. Angew. Chem., Int. Ed. 2007, 46, 926.
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Romesberg, F. E.; Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 5751.
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Collum, D.B.5
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64
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58049219220
-
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15N are 1 and 1/2, respectively.
-
15N are 1 and 1/2, respectively.
-
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65
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33646859403
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58049191883
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Dissolving the yellow solid with added N,N,N′, N′-tetramethylethylene-diamine (TMEDA) resulted in very complex mixtures. We suspect that TMEDA mediates reversal of the 1,4-addition, allowing other reactions to occur
-
Dissolving the yellow solid with added N,N,N′, N′-tetramethylethylene-diamine (TMEDA) resulted in very complex mixtures. We suspect that TMEDA mediates reversal of the 1,4-addition, allowing other reactions to occur.
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77
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58049199617
-
-
By contrast, the relatively weak acid hexamethyldisilazane converts dimer 5 to picoline 1.
-
By contrast, the relatively weak acid hexamethyldisilazane converts dimer 5 to picoline 1.
-
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58049197324
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Also see ref 9
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(i) Also see ref 9.
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Mixed condensation of heteroaryllithiums with heteroarenes: (a) Gros, P.; Fort, Y J. Chem. Soc., Perkin Trans. 1 1998, 3515.
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(a) Gros, P.; Fort, Y.; Caubere, P. J. Chem. Soc., Perkin Trans. 1 1997, 3597.
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