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1
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33748714441
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-
in press
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For one of us (A.d.M.) this is to be counted as Part 133 in the series, 'Cyclopropyl Building Blocks for Organic Synthesis': (a) For Part 132, see: Marradi, M.; Brandi, A.; Magull, J.; Schill, H.; de Meijere, A. Eur. J. Org. Chem. 2006, in press,
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(2006)
Eur. J. Org. Chem.
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Marradi, M.1
Brandi, A.2
Magull, J.3
Schill, H.4
De Meijere, A.5
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3
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33751287928
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in press (e-First, DOI: 10.1055/s-2006-941600)
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Tanguy, C.; Bertus, P.; Szymoniak, J.; Larionov, O. V.; de Meijere, A. Synlett 2006, in press (e-First, DOI: 10.1055/s-2006-941600).
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(2006)
Synlett
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Tanguy, C.1
Bertus, P.2
Szymoniak, J.3
Larionov, O.V.4
De Meijere, A.5
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4
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0034806165
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-
and references cited therein
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The well-known vinylcyclopropane-to-cyclopentene rearrangement is significantly accelerated by donor substituents like alkoxy and dialkylamino groups in the 2-position; compare with: (a) McGaffin, G.; Grimm, B.; Heinecke, U.; Michaelsen, H.; de Meijere, A.; Walsh, R. Eur. J. Org. Chem. 2001, 3559; and references cited therein,
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McGaffin, G.1
Grimm, B.2
Heinecke, U.3
Michaelsen, H.4
De Meijere, A.5
Walsh, R.6
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6
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0012974554
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The rearrangement of cyclopropylketimines, which is catalyzed by acids and known as the Cloke rearrangement, should also be accelerated by donor substituents: (a) Cloke, J. B. J. Am. Chem. Soc. 1929, 51, 1174.
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(1929)
J. Am. Chem. Soc.
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Cloke, J.B.1
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7
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0000835314
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de Meijere, A., Ed.; Thieme: Stuttgart
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(b) Review: Hudliky, T.; Becker, D. A.; Fan, R. L.; Kozhushkov, S. I. In Methods of Organic Chemistry, Houben-Weyl, Vol. E17c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, 2538.
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Methods of Organic Chemistry, Houben-Weyl
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Hudliky, T.1
Becker, D.A.2
Fan, R.L.3
Kozhushkov, S.I.4
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8
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0005825027
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and references cited therein
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(c) See also: Funke, C.; Es-Sayed, M.; de Meijere, A. Org. Lett. 2000, 2, 4249; and references cited therein.
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Org. Lett.
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Funke, C.1
Es-Sayed, M.2
De Meijere, A.3
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9
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0039354995
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Carbocyclic three-and four-membered ring compounds
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de Meijere, A., Ed.; Thieme: Stuttgart
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For reviews on vicinally donor-acceptor-substituted cyclopropanes see: (a) von Angerer, S. Carbocyclic Three-and Four-Membered Ring Compounds, In Methods of Organic Chemistry, Houben-Weyl, Vol. 17c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, 2121.
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Methods of Organic Chemistry, Houben-Weyl
, vol.17 C
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Von Angerer, S.1
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12
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0001310852
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(a) Shimada, S.; Hashimoto, Y.; Sudo, A.; Hasegawa, M.; Saigo, K. J. Org. Chem. 1992, 57, 7126.
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Shimada, S.1
Hashimoto, Y.2
Sudo, A.3
Hasegawa, M.4
Saigo, K.5
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16
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33748694435
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Angew. Chem. 2004, 116, 2723.
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18
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27144499189
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(b) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565.
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1242308377
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Wiedemann, S.; Rauch, K.; Savchenko, A.; Marek, I.; de Meijere, A. Eur. J. Org. Chem. 2004, 631.
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Wiedemann, S.1
Rauch, K.2
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Marek, I.4
De Meijere, A.5
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23
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0001539554
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The conversion of 3-oxoketimines into 2-hydroxy-5-arylpyrrolines has been reported, see: Chiu, P.-K.; Sammes, M. P. Tetrahedron 1988, 44, 3531.
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Tetrahedron
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Chiu, P.-K.1
Sammes, M.P.2
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24
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33748636515
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Jones, R. C. F.; Howard, K. J.; Nichols, J. R.; Snaith, J. S. J. Chem. Soc., Perkin Trans. 1 1998, 2061.
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Jones, R.C.F.1
Howard, K.J.2
Nichols, J.R.3
Snaith, J.S.4
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25
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33748708335
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note
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4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (PE-EtOAc, 9:1).
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26
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33748707295
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note
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13C NMR
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-
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27
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33748699921
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note
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+; found: 174.0918.
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28
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20544465179
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Huang, D.5
Holman, T.R.6
Toste, F.D.7
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29
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0034768614
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Vargiu, L.6
Murgioni, C.7
La Colla, P.8
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