Naphthaldehydeの電解還元反応

概要

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The electrolytic reduction mechanism of 1-naphthaldehyde and 2-naphthaldehyde was studied by means of potential scanning. The carbon atoms of formyl groups form the carbon anion radical in the region of the first step wave. Since the oxidation current is observed at the symmetrical positions to the carbon anion radical, it is conceivable that the reversible reaction has been observed in the region of the second step wave. Therefore, it is presumed that an irreversible reaction takes place and carbonanions are produced. In the electrolytic reduction of 1-naphthaldehyde and 2-naphthaldehyde, the carbon atoms of formyl groups forms carbon anion radicals first and carbanions later with the process of the reduction. Then, the electron state of the carbon and oxygen atoms in the formyl groups was investigated by LCAO-MO method. The carbon atoms of the formyl group in 1-naphthaldehyde can be considered rich in nucleophilic reactivity and those of 2-naphthaldehyde in radical reactivity. Since oxygen is negative electrically, the electrolytic reduction accompanies a nucleophilic addition reaction. The calculation results by LCAO-MO method support the reactivity.
公益社団法人日本薬学会の論文
1974-06-25