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It has been proposed by several examples that the epimerization promoted by TBAI (or TBAB) via nucleophilic displacement of the halide ion and/or base via keto-enol tautomerization.
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It has been proposed by several examples that the epimerization promoted by TBAI (or TBAB) via nucleophilic displacement of the halide ion and/or base via keto-enol tautomerization. Treweeke N.R., Hitchcock P.B., Pardoe D.A., and Caddick S. Chem. Commun. (2005) 1868
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Caddick S., Afonso C.A.M., Candeias S.X., Hitchcock P.B., Jenkins K., Murtagh L., Pardoe D., Santos A.G., Treweeke N.R., and Weaving R. Tetrahedron 57 (2001) 6589
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19
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33947412472
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note
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2 (10 mL × 2) and the combined extracts were washed with brine. The solvent was removed under reduced pressure and the crude material was purified by column chromatography to give a dihydroquinoxalinone.
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20
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33947360431
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note
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1d
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21
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85088738941
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note
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3, 400 MHz) 10a, 8.11 (or, 1H), 6.80-6.56 (m, 3H), 3.98 (q, J = 6.6 Hz, 1H), 3,83 (br, 1H), 2.25 (s, 3H), 1.46 (d, J = 7.2 Hz, 3H); 10b, 8.69 (br, 1H), 6.80-6.56 (m, 3H), 4.04 (q, J = 6.6 Hz, 1H), 3,71 (br, 1H), 2.17 (s, 3H), 1.49 (d, J = 6.8 Hz, 3H). {A figure is presented}
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