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1
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77955468137
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note
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The Hajos-Parrish-Eder-Sauer-Wiechert reaction is one of the most representative example leading to 5-6 and 6-6 fused rings:
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2
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77955468743
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German Patent DE 2,102,623
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Hajos, Z.G.; Parrish, D.R. German Patent DE 2,102,623, 1971.
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(1971)
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Hajos, Z.G.1
Parrish, D.R.2
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4
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77955466374
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German Patent DE 2,014,757
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Eder, U.; Sauer, G.; Wiechert, R. German Patent DE 2,014,757, 1971.
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(1971)
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Eder, U.1
Sauer, G.2
Wiechert, R.3
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5
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84981886574
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For a recent application in total synthesis, see: U. Eder, G. Sauer, and R. Wiechert Angew. Chem., Int. Ed. 10 1971 496 497
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Angew. Chem., Int. Ed.
, vol.10
, pp. 496-497
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Eder, U.1
Sauer, G.2
Wiechert, R.3
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6
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60149084818
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Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako, A. Nakazaki, and S. Kobayashi Angew. Chem. Int. Ed. 48 2009 1400 1403
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Angew. Chem. Int. Ed.
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Murata, Y.1
Yamashita, D.2
Kitahara, K.3
Minasako, Y.4
Nakazaki, A.5
Kobayashi, S.6
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7
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33947667037
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For reviews dealing with the synthesis and reactivity of allenes
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For reviews dealing with the synthesis and reactivity of allenes, see: K.M. Brummond, and J.E. DeForrest Synthesis 2007 795 818
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(2007)
Synthesis
, pp. 795-818
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Brummond, K.M.1
Deforrest, J.E.2
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9
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4544320494
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N. Krause, A.S.K. Hashmi, Wiley-VCH Weinheim
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N. Krause, A.S.K. Hashmi, Modern allene chemistry Vol. 1 and 2 2004 Wiley-VCH Weinheim
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Modern Allene Chemistry
, vol.12
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10
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60949108432
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For relevant references concerning the reactivity of allenoates
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For relevant references concerning the reactivity of allenoates, see: L.-P. Liu, B. Xu, and G.B. Hammond Org. Lett. 10 2008 3887 3890
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Org. Lett.
, vol.10
, pp. 3887-3890
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Liu, L.-P.1
Xu, B.2
Hammond, G.B.3
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17
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27144549330
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A.J. Mota, A. Klein, F. Wendling, A. Dedieu, and M. Miesch Eur. J. Org. Chem. 2005 4346 4358
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Eur. J. Org. Chem.
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Mota, A.J.1
Klein, A.2
Wendling, F.3
Dedieu, A.4
Miesch, M.5
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20
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0030458427
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For the reactivity of 2-methyl-1,3-cycloalkanediones tethered to electron-deficient functional groups
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For the reactivity of 2-methyl-1,3-cycloalkanediones tethered to electron-deficient functional groups, see: D. Schinzer, T. Blume, and P.G. Jones Angew. Chem., Int. Ed. Engl. 35 1996 2500 20502
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Angew. Chem., Int. Ed. Engl.
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Schinzer, D.1
Blume, T.2
Jones, P.G.3
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21
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0037007673
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J. Yamazaki, A.V. Bedekar, T. Watanabe, K. Tanaka, J. Watanabe, and K. Fuji Tetrahedron: Asymmetry 13 2002 729 734
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Tetrahedron: Asymmetry
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Yamazaki, J.1
Bedekar, A.V.2
Watanabe, T.3
Tanaka, K.4
Watanabe, J.5
Fuji, K.6
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24
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75749134566
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P. Geoffroy, M.-P. Ballet, S. Finck, E. Marchioni, C. Marcic, and M. Miesch Synthesis 2010 171 179
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Synthesis
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Geoffroy, P.1
Ballet, M.-P.2
Finck, S.3
Marchioni, E.4
Marcic, C.5
Miesch, M.6
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25
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77955471011
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note
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1H NMR spectra. Allenoate 11 was isolated as a mixture of two isomers bearing a cis ring junction (yield: 21%; ratio: 1/1.3) along with 1 isomer bearing a trans ring junction (34%).
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26
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77955472485
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Allenoate 11 bearing a trans ring junction and E allenoate was obtained by column chromatography of the crude mixture of allenoate. CCDC-705046 contains the supplementary crystallographic data for compound 11. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data-request/cif. CCDC-637164 contains the supplementary crystallographic data for compound 10. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif.
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27
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0344965589
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For oxetanes bearing an electrophilic exocyclic double bond
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For oxetanes bearing an electrophilic exocyclic double bond see: G. Ahlgren J. Org. Chem. 38 1973 1369-1374
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J. Org. Chem.
, vol.38
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Ahlgren, G.1
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32
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77955471098
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note
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The synthesis of the acetate derivative derived from acetylenic ω-ketoester 7 was also carried out but led to a complex mixture of inseparable isomers; therefore, the reactivity of the latter toward TBAF was not studied. On the other hand, the formation of the syn acetate derived from the acetylenic ω-ketoester 4 took place in less than 10% yield so that it's reactivity toward TBAF was also not studied.
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33
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77955469389
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note
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The 4 molecular sieves were activated by heating at 250°C/0.01 mm Hg for 12 h and then stored at room temperature under argon.
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35
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0000905636
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L.M. Weinstock, S. Karady, F.E. Roberts, A.M. Hoinowski, G.S. Brenner, T.B.K. Lee, W.C. Lumma, and M. Sletzinger Tetrahedron Lett. 46 1975 3979 3982
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Weinstock, L.M.1
Karady, S.2
Roberts, F.E.3
Hoinowski, A.M.4
Brenner, G.S.5
Lee, T.B.K.6
Lumma, W.C.7
Sletzinger, M.8
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36
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0037123426
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A. Padwa, J.D. Ginn, S.K. Bur, C.K. Eidell, and S.M. Lynch J. Org. Chem. 67 2002 3412 3424
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Padwa, A.1
Ginn, J.D.2
Bur, S.K.3
Eidell, C.K.4
Lynch, S.M.5
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