Y. Kurauchi, Hideo Nobuhara, K. Ohga
Mar 1, 1986
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The irradiation of aqueous solutions of 1-methyl-2-phenyl-1-pyrrolinium perchlorate (1) in the presence of α-hydroxyalkanoate anions led to the formation of 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 the carboxylato groups of alkanoates to the excited singlet state of 1 (1S1), followed by an efficient decarboxylation. Furthermore, the photoreaction of 1 with ethoxyacetate was found to give a 2-(ethoxymethyl)pyrrolidine adduct in preference to the reduction product. For photoreactions with 2-mercaptopropionate and α-amino acids, the reduction product was detected. N-Acetylglycinate gave a 2-(acetylaminomethyl)pyrrolidine adduct in fairly high yield (80%). The features of these photoreactions with α-heteroatom-substituted alkanoates are discussed in terms of fluorescence-quenching efficiencies and the properties of radicals formed through electron transfer...