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Mechanisms of importance in synthesis
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(a) Bailey, W. F.; Ovaska, T. V. Mechanisms of Importance in Synthesis. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273.
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By way of comparison, the half-time for cyclization of the parent 5-hexenyllithium in the presence of TMEDA is ∼6 min at -30 °C. See: Bailey, W. F.; Carson, M. W. J. Org. Chem. 1998, 63, 361.
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0242497688
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note
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7 it is necessary to conduct the lithium-bromine exchange in a solvent system that contains a dialkyl ether, it is not possible to prepare the aryllithium in good yield in a pure hydrocarbon solvent.
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24
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0000057455
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6d Indeed, intramolecular coordination of the lithium atom with the remote π-bond in the ground state of 5-hexenyllithium has been experimentally confirmed; see: Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
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37049068007
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6d Indeed, intramolecular coordination of the lithium atom with the remote π-bond in the ground state of 5-hexenyllithium has been experimentally confirmed; see: Rölle, T.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. 2 1995, 1953.
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