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For a Ru-catalyzed example, see
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0024520675
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For the initial addition of a tributyltin radical to a triple bond see: a
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b) For the reverse regioselectivity, see also: Z. Wang, X. Lu, Tetrahedron 1995, 51, 2639.
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45
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T. Cohen, H. Gibney, R. Ivanov, E. A.-H. Yeh, I. Marek, D. P. Curran, J. Am. Chem. Soc. 2007, 129, 15405.
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49
-
-
53749086127
-
-
The assignments are based on the chemical shifts of the vinylic proton being more shielded in the Z isomer than in the E isomer: 6.59 ppm in (E)-2/5.59 ppm in (Z)-2; 6.42 ppm in (E)-3/5.73 ppm in (Z)-3; 6.27 ppm in (E)-4; 6.43 ppm in (E)-6.
-
The assignments are based on the chemical shifts of the vinylic proton being more shielded in the Z isomer than in the E isomer: 6.59 ppm in (E)-2/5.59 ppm in (Z)-2; 6.42 ppm in (E)-3/5.73 ppm in (Z)-3; 6.27 ppm in (E)-4; 6.43 ppm in (E)-6.
-
-
-
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52
-
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1942496535
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-
For recent investigations, see: c
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For recent investigations, see: c) J. Lewinski, Z. Ochal, E. Bojarski, E. Tratkiewicz, I. Justyniak, J. Lipkowski, Angew. Chem. Int. Ed. 2003, 42, 4643;
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0346191943
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d) J. Lewinski, M. Wojciech, J. Lipkowski, I. Justyniak, J. Am. Chem. Soc. 2003, 125, 12698.
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54
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53749098743
-
-
According to a referee comment, the formation of G from A and similarly the formation of D from B might involve electron transfer from dialkylzinc rather than direct bimolecular homolytic substitution.
-
According to a referee comment, the formation of G from A and similarly the formation of D from B might involve electron transfer from dialkylzinc rather than direct bimolecular homolytic substitution.
-
-
-
-
55
-
-
0000679160
-
-
An alternative explanation would involve an iodine/zinc exchange between iodide 3 and diethylzinc. A reduction pathway involving iodine/magnesium exchange has been proposed for EtMgBr-promoted radical cyclization of iodoacetals, see: A. Inoue, H. Shinokubo, K. Oshima, Org. Lett. 2000, 2, 651
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An alternative explanation would involve an iodine/zinc exchange between iodide 3 and diethylzinc. A reduction pathway involving iodine/magnesium exchange has been proposed for EtMgBr-promoted radical cyclization of iodoacetals, see: A. Inoue, H. Shinokubo, K. Oshima, Org. Lett. 2000, 2, 651.
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33947701427
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58
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53749096165
-
-
2Zn and only 5 equiv. of tBuI.
-
2Zn and only 5 equiv. of tBuI.
-
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60
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0042232501
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b) R. Gómez-Balderas, M. L. Coote, D. J. Henry, H. Fischer, L. Radom, J. Phys. Chem. A 2003, 107, 6082;
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62
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0001049972
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Knochel has demonstrated that RZnI derivatives tolerate the presence of acidic protons, in particular those of terminal non-activated alkynes, see
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Knochel has demonstrated that RZnI derivatives tolerate the presence of acidic protons, in particular those of terminal non-activated alkynes, see: H. P. Knoess, M. T. Furlong, M. J. Rozema, P. Knochel, J. Org. Chem. 1991, 56, 5974.
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|