Electron-Transfer-Initiated Photoreactions of 1-Methyl-2-phenyl-1-pyrrolinium Perchlorate with α-Heteroatom-Substituted Alkanoate Anions

摘要: The irradiation of aqueous solutions 1-methyl-2-phenyl-1-pyrrolinium perchlorate (1) in the presence α-hydroxyalkanoate anions led to formation 2-(hydroxyalkyl)pyrrolidine adducts and a reduction product, 1-methyl-2-phenylpyrrolidine. Mechanistic studies demonstrated that photoaddition reactions were induced by one-electron transfers from carboxylato groups alkanoates excited singlet state 1 (1S1), followed an efficient decarboxylation. Furthermore, photoreaction with ethoxyacetate was found give 2-(ethoxymethyl)pyrrolidine adduct preference product. For photoreactions 2-mercaptopropionate α-amino acids, product detected. N-Acetylglycinate gave 2-(acetylaminomethyl)pyrrolidine fairly high yield (80%). features these α-heteroatom-substituted are discussed terms fluorescence-quenching efficiencies properties radicals formed through electron transfer...