T. Fuchigami, T. Iwaoka, T. Nonaka
Jul 1, 1980
Citations
0
Influential Citations
11
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Intramolecular N,N-coupling by the electrochemical oxidation of cyclic and open-chain diamines such as 3,3,7,7-tetraethylperhydro-1,5-diazocine (1) and N,N-dimethyl-2,2-diethyl-1,3-diaminopropane (2) was investigated with the use of platinum, silver, nickel, and carbon anodes. In the case of 1, 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 2, 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 1 and 2 was studied by using sodium peroxodisulfate and lead tetraacetate.