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- W2085134669 abstract "3-Pyridinecarboxaldehyde (7) has been studied as a model system for superelectrophilic activation. When compound 7 is compared with benzaldehyde (3) in acid-catalyzed condensation reactions with arenes, 7 is more reactive than 3. Compound 7 reacts with chlorobenzene, o-dichlorobenzene, or nitrobenzene in CF3SO3H (triflic acid, TfOH) to give diaryl-3-pyridylmethanes, while 3 does not react with these deactivated arenes in TfOH. Moreover, 7 reacts with benzene in solutions as weakly acidic as Ho = −9, while 3 requires acidity in the range of Ho = −11.5 to −14 to reach a comparable level of electrophilic reactivity. Compound 7 was studied in acidic solution by 13C NMR, and the diprotonated, dicationic species was observed at −60 °C in a solution of FSO3H−SbF5." @default.
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- W2085134669 date "1999-09-10" @default.
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- W2085134669 title "3-Pyridinecarboxaldehyde: A Model System for Superelectrophilic Activation and the Observation of a Diprotonated Electrophile" @default.
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- W2085134669 doi "https://doi.org/10.1021/jo9824908" @default.
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