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0000661691
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Adams, R., Ed.; Wiley: New York
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Jones, R.G.1
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12
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33744761233
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note
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Introduction of a protecting group was necessary in light of the prospected reactions of 2 with aliphatic halides.
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13
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14844291428
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(a) Chinchilla, R.; Nájera, C.; Yus, M. Tetrahedron 2005, 61, 3139-3176.
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Chinchilla, R.1
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0037503118
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Rappoport, Z., Marek, I., Eds.; Wiley: New York
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(b) The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: New York, 2004.
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(b) Dastan, A.; Uzundumlu, E.; Balci, M.; Fabris, F.; De Lucchi, O. Eur. J. Org. Chem. 2004, 183-192.
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0033918041
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22
-
-
33744760268
-
-
note
-
Easily available in four steps from commercial 1,3-cyclopentanedione, as depicted in Scheme 2.
-
-
-
-
23
-
-
0003515129
-
-
E. Arnold: London
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Vedeneyev, V. I.; Gurvich, L. V.; Kondrat'yev, V. N.; Medvedev, V. A.; Fraukevich, Y. L. Bond Energies, Ionization Potentials and Electron Affinities; E. Arnold: London, 1966.
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Gurvich, L.V.2
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Gilman, H.; Langham, W.; Moore, F. W. J. Am. Chem. Soc. 1940, 62, 2327-2335.
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Langham, W.2
Moore, F.W.3
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25
-
-
33744761903
-
-
note
-
2 (30 equiv), pentane, 5 h, room temperature; 85% overall yield.
-
-
-
-
28
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-
0029919682
-
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and references therein
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Mongin, F.; Desponds, O.; Schlosser, M. Tetrahedron Lett. 1996, 37, 2767-2770 and references therein.
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Mongin, F.1
Desponds, O.2
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29
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33744756089
-
-
note
-
In contrast to 1-lithio-2-bromocyclopentene which is relatively stable up to 25 °C, 1-lithio-2-bromocyclohexene is reported to lose LiBr even at ≤ 120 °C, hampering the extension of this methodology to 1,2- dihalocyclohexenes.
-
-
-
-
30
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-
84957159009
-
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For studies on the stability of different 1-lithio-2-halocycloalkenes, see: (a) Wittig, G.; Mayer, U. Chem. Ber. 1963, 96, 329-341.
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Wittig, G.1
Mayer, U.2
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0001034792
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(c) Wittig, G.; Weinlich, J.; Wilson, E. R. Chem. Ber. 1965, 98, 458-470.
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Wittig, G.1
Weinlich, J.2
Wilson, E.R.3
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