Electrochemical generation of unstable nitrogen species. 4. Electrochemical and chemical oxidation of cyclic and open-chain diamines. The formation of cyclic hydrazine derivatives.

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概要

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• Intramolecular N,N-coupling by the electrochemical oxidation of cyclic and open-chain diamines such as 3,3,7,7-tetraethylperhydro-1,5-diazocine (<B>1</B>) and <I>N</I>,<I>N</I>-dimethyl-2,2-diethyl-1,3-diaminopropane (<B>2</B>) was investigated with the use of platinum, silver, nickel, and carbon anodes. In the case of <B>1</B>, cyclic hydrazine derivatives, 3,3,7,7-tetraethyl-1,5-diazabicyclo[3.3.0]octane and 1-(2-ethyl-2-formylbutyl)-4,4-diethyl-4,5-dihydropyrazole, were formed in high current efficiency. In the case of <B>2</B>, the corresponding hydrazines, 1,2-dimethyl-4,4-diethylpyrazolidine and 1-methyl-3,3-diethyl-4,5-dihydropyrazole, were obtained in low current efficiency, because C–N bond cleavage took place before N,N-coupling. A carbon anode was found to be effective for N,N-coupling of such diamines. Chemical oxidative N,N-coupling of <B>1</B> and <B>2</B> was studied by using sodium peroxodisulfate and lead tetraacetate.

• 公益社団法人 日本化学会の論文

著者

• Nonaka Tsutomu

  Department Of Electric Chemistry Tokyo Institute Of Technology

• Fuchigami Toshio

  Department Of Electronic Chemistry Tokyo Institute Of Technology

• Sekine Taro

  Department of Electronic Chemistry, The Graduate School at Nagatsuta, Tokyo Institute of Technology

• SEKINE TARO

  Department of Chemical Engineering, Niigata University

• Iwaoka Tomoyasu

  Department of Electronic Chemistry, The Graduate School at Nagatsuta, Tokyo Institute of Technology

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