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Three examples of aziridine ring opening with ortho-fluoro substituted aryl magnesium halide reagents are described in: However, these examples all involved bis-fluorinated arenes and experimental details are not provided
-
Three examples of aziridine ring opening with ortho-fluoro substituted aryl magnesium halide reagents are described in:. Zhu G.-D., Ghandi V.B., Gong J., Thomas S., Woods K.W., Song X., Li T., Diebold R.B., Luo Y., Liu X., Guan R., Klinghofer V., Johnson E.F., Bouska J., Olson A., Marsh K.C., Stoll V.C., Mamo M., Polakowski J., Campbell T.J., Martin R.L., Gintant G.A., Penning T.D., Li Q., Rosenberg S.H., and Giranda V.L. J. Med. Chem. 50 (2007) 2990-3003 However, these examples all involved bis-fluorinated arenes and experimental details are not provided
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Zhu, G.-D.1
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Johnson, E.F.13
Bouska, J.14
Olson, A.15
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Polakowski, J.19
Campbell, T.J.20
Martin, R.L.21
Gintant, G.A.22
Penning, T.D.23
Li, Q.24
Rosenberg, S.H.25
Giranda, V.L.26
more..
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33
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41449083248
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For a detailed examination of the decomposition of 2-chloro-6-fluorophenyllithium into benzynes, see:
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For a detailed examination of the decomposition of 2-chloro-6-fluorophenyllithium into benzynes, see:. Riggs J.C., Ramirez A., Cremeens M.E., Bashore C.G., Candler J., Wirtz M.C., Coe J.W., and Collum D.B. J. Am. Chem. Soc. 130 (2008) 3406-3412
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Schlosser, M.1
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44
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33744928097
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For an example of a reaction between a 2,6-dibromophenyllithium species and an epoxide using toluene as solvent, see:
-
For an example of a reaction between a 2,6-dibromophenyllithium species and an epoxide using toluene as solvent, see:. Okano K., Tokuyama H., and Fukuyama T. J. Am. Chem. Soc. 128 (2006) 7136-7137
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Okano, K.1
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-
45
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33644638474
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Aryl iodides were generated via deprotonation of the corresponding 1,3-dihalobenzenes with LDA and quenching of the aryllithium intermediate with iodine. For the syntheses of 1-bromo-3-chloro-2-iodobenzene and 1-bromo-3-fluoro-2-iodobenzene, the aryllithium intermediate was treated with zinc chloride prior to the iodine quench, according to the procedure of:
-
Aryl iodides were generated via deprotonation of the corresponding 1,3-dihalobenzenes with LDA and quenching of the aryllithium intermediate with iodine. For the syntheses of 1-bromo-3-chloro-2-iodobenzene and 1-bromo-3-fluoro-2-iodobenzene, the aryllithium intermediate was treated with zinc chloride prior to the iodine quench, according to the procedure of:. Menzel K., Fisher E.L., DiMichele L., Frantz D.E., Nelson T.D., and Kress M.H. J. Org. Chem. 71 (2006) 2188-2191
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Menzel, K.1
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Nelson, T.D.5
Kress, M.H.6
-
46
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61749086951
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-
note
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6, 23 °C) δ ppm 7.58 (d, J = 7.9 Hz, 2H), 7.15-7.28 (m, 6H), 7.04 (t, J = 8.1 Hz, 1H), 6.67 (d, J = 9.5 Hz, 1H), 4.06-4.16 (m, 1H), 3.15 (dd, J = 13.4, 9.5 Hz, 1H), 3.03 (dd, J = 13.4, 4.6 Hz, 1H), 2.91 (dd, J = 13.7, 9.5 Hz, 1H), 2.72 (dd, J = 13.6, 5.3 Hz, 1H), 1.17 (s, 9H).
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