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KMID : 1059519910350010070
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Journal of the Korean Chemical Society
1991 Volume.35 No. 1 p.70 ~ p.77
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Synthesis of 1-Benzyl-4-Iodomethyl-2-Azetidinone and Electrochemical Reduction on the Iodo Grou
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Kim Il-Kwang
Lee Young-Haeng
Lee Chai-Ho
Chai Kyu-Yun
Kim Youn-Geun
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Abstract
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1-Benzyl-4-iodomethyl-2-azetidinone(BIMA) was synthesized and its electrochemical reduction was investigated by direct current, differential pulse polarography, cyclic voltammetry and controlled potential coulometry. The irreversible two electron transfer on reductive dehalogenation of iodo group proceeded to form 1-benzyl-4-methyl-2-azetidinone by EEC electrode reaction mechanism at the first reduction step(-1.35 volts vs. Ag-AgCl). The polarographic reduction waves separated into two reduction steps due to anionic surfactant (sodium lauryl sulfate) effects, while the waves were shifted to the positive potential as the concentration of cationic surfactant (cetyltrimethylammonium bromide) increased. Upon the basis of results on the product analysis and interpretation of polarogram with pH variable, EEC electrochemical reaction mechanism was suggested.
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