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WO 109456 A2
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The energy gaps between the HOMO of phenyl nitrile oxide and the LUMO of crotonates are 1.5-2.5 eV smaller than the gaps between the HOMO of crotonates and the LUMO of nitrile oxide. The calculated HOMO coefficients for the 1,3-dipole are 42 for ArCNO and 27 for ArCNO. For related regioselectivity models, see
-
The energy gaps between the HOMO of phenyl nitrile oxide and the LUMO of crotonates are 1.5-2.5 eV smaller than the gaps between the HOMO of crotonates and the LUMO of nitrile oxide. The calculated HOMO coefficients for the 1,3-dipole are 42 for ArCNO and 27 for ArCNO. For related regioselectivity models, see: A. Rastelli, R. Gandolfi, and M.S. Amadè J. Org. Chem. 63 1998 7425
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0034644620
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25
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51849084295
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Please see Supplementary data for details. The observed regioselectivities were independent on the geometry of the dipolarophile olefin. The use of methyl 2-chloromethylcrotonate affords the isoxazole with opposite regioselectivity, highlighting the effect of the trifluoromethyl group
-
Please see Supplementary data for details. The observed regioselectivities were independent on the geometry of the dipolarophile olefin. The use of methyl 2-chloromethylcrotonate affords the isoxazole with opposite regioselectivity, highlighting the effect of the trifluoromethyl group: J. Lasri, S. Mukhopadhyay, and M. Adília Januárip Charmier J. Heterocycl. Chem. 45 2008 1385
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While this manuscript was in preparation, a similar transformation was reported
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While this manuscript was in preparation, a similar transformation was reported: D.C. Schmitt, L. Lam, and J.S. Johnson Org. Lett. 13 2011 5136
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Enolates of 1-oxo-3,3,3-trifluoromethyl compounds undergo extremely facile elimination of fluoride: see
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Enolates of 1-oxo-3,3,3-trifluoromethyl compounds undergo extremely facile elimination of fluoride: see K. Mikami, and Y. Itoh Chemical Record 6 2006 1
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-
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