Abstract
Abstract The photochemical reactions of 2-quinolinecarbonitriles with alcohols, diethyl ether, or aliphatic carboxylic acids in an atmosphere of oxygen or nitrogen were found to result in the replacement of the cyano group by 1-hydroxyalkyl, 1-ethoxyethyl, or alkyl group. However, the irradiation of 2-quinolinecarbonitrile in an alcoholic solvent except for the case of tert-butyl alcohol under a nitrogen atmosphere gave an unidentified substance (probably, a certain triazapentaphene) in addition to the photosubstitution product. The photoinduced substitution reaction found in the present experiment was revealed to proceed through the excited singlet state of 2-quinolinecarbonitrile, whereas the lowest triplet state was responsible for the formation of an unidentified substance in a deaerated alcohol.
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