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 CF 3 SO 3 H (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 H o = −9, while 3 requires acidity in the range of H o = −11.5 to −14 to reach a comparable level of electrophilic reactivity. Compound 7 was studied in acidic solution by 13 C NMR, and the diprotonated, dicationic species was observed at −60 °C in a solution of FSO 3 H−SbF 5 .
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Klumpp et al. (1999) studied this question.
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