Electron-transfer-initiated photoreactions of 1-methyl-2-phenyl-1-pyrrolinium perchlorate with .ALPHA.-heteroatom-substituted alkanoate anions.
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概要
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The irradiation of aqueous solutions of 1-methyl-2-phenyl-1-pyrrolinium perchlorate (<B>1</B>) 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 <B>1</B> (<B>1</B><SUP>S<SUB>1</SUB></SUP>), followed by an efficient decarboxylation. Furthermore, the photoreaction of <B>1</B> 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. <I>N</I>-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 transfers to <B>1</B><SUP>S<SUB>1</SUB></SUP>.
- 公益社団法人 日本化学会の論文
著者
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Ohga Kazuya
Department Of Applied Chemistry Faculty Of Engineering Oita University
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Kurauchi Yoshiaki
Department Of Applied Chemistry Faculty Of Engineering Oita University
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Nobuhara Hideo
Department of Environmental Chemistry and Engineering, Faculty of Engineering, Oita University
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