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- W4294167789 abstract "NaNO 2 /K 2 S 2 O 8 -mediated deformylative oximation ring contraction (DORC) or deformylative alkoxyoximation (DAO) bifunctionalization reactions of 3-formylchromones under benign conditions are described. The DORC of 3-formylchromones takes place in the presence of K 2 S 2 O 8 , NaNO 2 and H 2 O to give 2-hydroxyiminobenzofuran-3-ones, while the DAO features the bifunctionalization of 3-formylchromones in the presence of K 2 S 2 O 8 , NaNO 2 and ROH (alcohol) to afford 2-alkoxy-3-(hydroxyimino)chromanones. The preliminary mechanistic studies indicate that NO + NO 3 − (one form of NO 2 radical dimer) initially adds to the electron-rich C 3 -site of 3-formylchromones to form a cationic intermediate, followed by attack of a nucleophile such as H 2 O or ROH to form a hemiacetal or acetal intermediate. Subsequently, the hemiacetal undergoes a tandem deformylation, ring-opening and ring-closing process to give 2-hydroxyiminobenzofuran-3-ones, while the acetal undergoes deformylation to give 2-alkoxy-3-(hydroxyimino)chromanones. • Reaction of 3-formylchromones, NaNO 2 , and H 2 O or alcohols afforded the products 2-hydroxyiminobenzofuran-3-ones or 2-alkoxy-3-(hydroxyimino)chromanones." @default.
- W4294167789 created "2022-09-02" @default.
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- W4294167789 date "2022-10-01" @default.
- W4294167789 modified "2023-09-27" @default.
- W4294167789 title "NaNO2/K2S2O8-mediated selective transformation of 3-formylchromones to 2-hydroxyiminobenzofuran-3-ones and 2-alkoxy-3-(hydroxyimino)chromanones" @default.
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- W4294167789 doi "https://doi.org/10.1016/j.tet.2022.133010" @default.
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