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33845243875
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note
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These oxepine products decomposed slowly on untreated silica gel.
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27
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33845258888
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note
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1H NMR coupling constants associated with the α-proton in oxepine 7 provided the relative stereochemical identity of the syn diastereomer. X-ray crystal analysis of the 3,5-dinitrobenzoyl ester of oxepine 8 provided the relative stereochemical identity of the anti diastereomer.
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28
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22244468979
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For a computational comparison of the Cope rearrangement of divinyl oxirane and cyclopropane, see: (a) Zora, M. J. Org. Chem. 2005, 70, 6018.
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33845257260
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note
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Varian's NOESY1D (DPFGSE NOE) experiments for measurement of transient NOEs are generally lower in intensity than steady-state NOE values.
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37
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33845261750
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note
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In contrast to the systems with a methylene group, perhaps the epoxide oxygen allows for a more facile electrocyclic fragmentation of the C3-C4 bond in the C1-C2 retention pathway (Scheme 4).
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