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33646931079
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Taken in part from the Ph.D. thesis of Mary Dosch Doubleday, University of Pittsburgh, 1991.
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33646927392
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Block E. (Ed), VCH, New York, NY Chapter 7
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Cohen T. In: Block E. (Ed). Heteroatom Chemistry (1990), VCH, New York, NY 129-142 Chapter 7
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(1990)
Heteroatom Chemistry
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Cohen, T.1
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Cooksey J., Gunn A., Kocienski P.J., Kuhl A., Uppal S., Christopher J.A., and Bell R. Org. Biomol. Chem. 2 (2004) 1719-1731
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(2004)
Org. Biomol. Chem.
, vol.2
, pp. 1719-1731
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Cooksey, J.1
Gunn, A.2
Kocienski, P.J.3
Kuhl, A.4
Uppal, S.5
Christopher, J.A.6
Bell, R.7
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Yanagisawa A., Ogasawara K., Yasue K., and Yamamoto H. J. Chem. Soc., Chem. Commun. (1996) 367-368
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(1996)
J. Chem. Soc., Chem. Commun.
, pp. 367-368
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Yanagisawa, A.1
Ogasawara, K.2
Yasue, K.3
Yamamoto, H.4
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41
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Ribeiro C.M.R., Demelo S.J., Bonin M., Quirion J.C., and Husson H.P. Tetrahedron Lett. 35 (1994) 7227-7230
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 7227-7230
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Ribeiro, C.M.R.1
Demelo, S.J.2
Bonin, M.3
Quirion, J.C.4
Husson, H.P.5
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0002397490
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Krief A., Hobe M., Badaoui E., Bousbaa J., Dumont W., and Nazih A. Synlett (1993) 707-709
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(1993)
Synlett
, pp. 707-709
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Krief, A.1
Hobe, M.2
Badaoui, E.3
Bousbaa, J.4
Dumont, W.5
Nazih, A.6
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Saá J.M., Ballester P., Deyá P.M., Capó M., and Garcías X. J. Org. Chem. 61 (1996) 1035-1046
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(1996)
J. Org. Chem.
, vol.61
, pp. 1035-1046
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Saá, J.M.1
Ballester, P.2
Deyá, P.M.3
Capó, M.4
Garcías, X.5
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The superior versatility of compounds containing the phenylthio group as substrates for reductive lithiation arises from their almost unique ease of construction, particularly by methods involving C-C bond formation but also by the ability of the phenylthio group to enter a molecule as a nucleophile, electrophile, or radical. In addition, the substrates are almost always able to withstand the powerful nucleophiles/bases that are present in the reductive lithiation conditions. For example, alkyl halides, sulfates, sulfonates, etc. are subject to ready nucleophilic substitution, but most seriously to base induced elimination, thus limiting their use largely to the preparation of primary alkyllithiums unless an aryl or vinyl group is present to increase the rate of the reductive lithiation and favor it over competing processes.
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Various aryl-substituted N,N-dimethylanilines also decompose to aryllithiums but at far higher temperatures.
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Rappoport Z., and Marek I. (Eds), Wiley, Chichester, UK Chapter 11
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Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, Chichester, UK Chapter 11
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(2004)
The Chemistry of Organolithium Compounds
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Yus, M.1
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At least one other group has mentioned this assertion in explanation of their use of the CA method:
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At least one other group has mentioned this assertion in explanation of their use of the CA method:. Manteca I., Etxarri B., Ardeo A., Arrasate S., Osante I., Sotomayor N., and Lete E. Tetrahedron 54 (1998) 12361-12378
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(1998)
Tetrahedron
, vol.54
, pp. 12361-12378
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Manteca, I.1
Etxarri, B.2
Ardeo, A.3
Arrasate, S.4
Osante, I.5
Sotomayor, N.6
Lete, E.7
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It is known that alkyllithiums such as 12 tend to exist at equilibrium in the cis configuration.
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It is known that alkyllithiums such as 12 tend to exist at equilibrium in the cis configuration. Evans D.A., Andrews G.C., and Buckwalter B. J. Am. Chem. Soc. 96 (1974) 5560-5561
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(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 5560-5561
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Evans, D.A.1
Andrews, G.C.2
Buckwalter, B.3
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Rappoport Z., and Marek I. (Eds), Wiley, New York, NY Chapter 15
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Strohmann C., and Schildbach D. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds (2004), Wiley, New York, NY Chapter 15
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(2004)
The Chemistry of Organolithium Compounds
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Schildbach, D.2
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