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6
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F. G. Bordwell, G. E. Drucker. H. E. Fried, J. Org. Chem. 1981, 46, 632-635, and references therein;
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-
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-
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7
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0003961339
-
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For an account of the earlier results see:, Academic Press. New York
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c) For an account of the earlier results see: D. J. Cram, Fundamentals of Carbanion Chemistry. Academic Press. New York. 1965.
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Fundamentals of Carbanion Chemistry
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Cram, D.J.1
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8
-
-
34250683554
-
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pK of polyhalogenated benzenes: a ref. [3a];
-
pK of polyhalogenated benzenes: a) ref. [3a];
-
-
-
-
9
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0000068345
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benzyl-silanes
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b) A. Streitwieser, F. Abu-Hasanyan, A. Neuhaus, F. Brown, J. Org. Chem. 1996, 61. 3151-3154; benzyl-silanes:
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Streitwieser, A.1
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10
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33751385140
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benzyl and fluorenyl hydrocarbons: 1993
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c) A. Streitwieser, L. Xie, P. Wang, S. M. Bachrach. J. Org. Chem. 1993, 58, 1778-1784; benzyl and fluorenyl hydrocarbons:
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Xie, L.2
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0001100546
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d) A. Streitwieser, J. C. Ciula, J. A. Krom. G. Thiele, J. Org. Chem. 1991, 50, 1074-1076;
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Streitwieser, A.1
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Thiele, G.4
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12
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33845279339
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and references therein
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e) M. J. Kaufman, S. Gronert, A. Streitwieser, Jr, J. Am. Chem. Soc. 1988, 110, 2829-2835, and references therein.
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Kaufman, M.J.1
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13
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0001516773
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14
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-
0001388587
-
-
This approach is based on the pioneering work of Applequist and Dessy who established that halogen-Li and Hg-Mg exchange equilibria could be used to measure the relative stabilities of simple alkyl, alkenyl and aryllithium or magnesium reagents: a D. E. Applequist, D. F. O'Brien, J. Am. Chem. Soc. 1963, 85, 743-748;
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This approach is based on the pioneering work of Applequist and Dessy who established that halogen-Li and Hg-Mg exchange equilibria could be used to measure the relative stabilities of simple alkyl, alkenyl and aryllithium or magnesium reagents: a) D. E. Applequist, D. F. O'Brien, J. Am. Chem. Soc. 1963, 85, 743-748;
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15
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33947335376
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20
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33845378372
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Fraser, R.R.1
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22
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34250674548
-
-
eq was obtained using a temperature of 223 K.
-
eq was obtained using a temperature of 223 K.
-
-
-
-
26
-
-
34250638314
-
-
The carbamoyloxy group used in this series was Cby because we observed mixtures of products when using the N,N-diisopropylcarbamate (Cb) group
-
The carbamoyloxy group used in this series was Cby because we observed mixtures of products when using the N,N-diisopropylcarbamate (Cb) group.
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27
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0001481464
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Eds, E. Buncel, T. Durst, Elsevier-North Holland, Amsterdam, Part A, pp
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34
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0000584326
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When an organolithium compound undergoes Sn-Li exchange with an unsymmetrical tetraalkylstannane the group that gets displaced from the stannane is the one that leads to the most stable anion, but if anion 7j and MeLi (the two possible leaving groups in the Sn-Li exchange of stannane 8j with organolithium compounds) have similar stabilities, then 7j can displace MeLi from stannane 8j to provide mixed stannane 10, beside the expected products: a) R. J. Linderman, A. Ghannam, J. Am. Chem. Soc. 1990, 112, 2392-2398
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When an organolithium compound undergoes Sn-Li exchange with an unsymmetrical tetraalkylstannane the group that gets displaced from the stannane is the one that leads to the most stable anion, but if anion 7j and MeLi (the two possible leaving groups in the Sn-Li exchange of stannane 8j with organolithium compounds) have similar stabilities, then 7j can displace MeLi from stannane 8j to provide mixed stannane 10, beside the expected products: a) R. J. Linderman, A. Ghannam, J. Am. Chem. Soc. 1990, 112, 2392-2398.
-
-
-
-
35
-
-
34250657701
-
-
pK of benzene = 39.5, see r f. [3a];
-
a) pK of benzene = 39.5, see r f. [3a];
-
-
-
-
36
-
-
34250687599
-
-
pK of benzene = 41. see ref. [7c].
-
b) pK of benzene = 41. see ref. [7c].
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37
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H. J. Reich, W. S. Goldenberg, A. W. Sanders, K. L. Jantzi, C. C. Tzschucke, J. Am. Chem. Soc. 2003, 125, 3509-3521, and references therein;
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39
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4243093686
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S. Gronert, A. Streitwieser, J. Am. Chem. Soc. 1988, 110, 2843-2847. and references therein;
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41
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0001342138
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P. J. A. Geurink, G. W. Klumpp. J. Am. Chem. Soc. 1986, 108, 538-539;
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44
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0035820016
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The effect of four-membered ring chelation by Li-O interaction cannot be measured in this system since the corresponding organolithium compound (11n, R, MeO) undergoes elimination as soon as it is formed: M.I. Calaza, M. R. Paleo, F. J. Sardina, J. Am. Chem. Soc. 2001, 123, 2095-2096
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The effect of four-membered ring chelation by Li-O interaction cannot be measured in this system since the corresponding organolithium compound (11n, R = MeO) undergoes elimination as soon as it is formed: M.I. Calaza, M. R. Paleo, F. J. Sardina, J. Am. Chem. Soc. 2001, 123, 2095-2096.
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46
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0040921308
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34250613990
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An approximate acidity scale can be derived from these data that should be of value in the planning of syntheses involving organolithium species compound/pTC, 9a/39.2, 9b/39.2, 9c/36.8-36.7, 9d/ 37.3-37.2. 9e/36.0, 9f/33.0, 9g/38.8, 9h/38.8, 91/38.8, 9J/38.8, 9k/39.1. 91/38.8. 9m/>42.7; 11a-H/37.1, 11b-H/36.3. 11c-H/39.3, 11d-H/ 36.7-36.8. 11e-H/38.8, 11f-H/37.0, 11g-H/37.4, 11h-H/38.4, 11i-H/ 37.4, 11j-H/36.7-36.8, 11k-H/36.8, 111-H/38.8, 11m-H/38.4; 13a-H/ 32.3-32.2, 13b-H/32.8-32.7, 13c-H/32.2, 13d-H/33.2, 13e-H/33.633.5
-
An approximate acidity scale can be derived from these data that should be of value in the planning of syntheses involving organolithium species (compound/pTC): 9a/39.2, 9b/39.2, 9c/36.8-36.7, 9d/ 37.3-37.2. 9e/36.0, 9f/33.0, 9g/38.8, 9h/38.8, 91/38.8, 9J/38.8, 9k/39.1. 91/38.8. 9m/>42.7; 11a-H/37.1, 11b-H/36.3. 11c-H/39.3, 11d-H/ 36.7-36.8. 11e-H/38.8, 11f-H/37.0, 11g-H/37.4, 11h-H/38.4, 11i-H/ 37.4, 11j-H/36.7-36.8, 11k-H/36.8, 111-H/38.8, 11m-H/38.4; 13a-H/ 32.3-32.2, 13b-H/32.8-32.7, 13c-H/32.2, 13d-H/33.2, 13e-H/33.633.5.
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