カルボン酸塩化物中におけるα, α'-アゾビスイソブチロニトリルの分解反応

抄録

Reactions of 1-cyano-1-methylethyl radicals produced by the decomposition of α, α'-azobisisobutyronitrile were investigated in oxalyl, acetyl and benzoyl chlorides. In oxalyl chloride, a compound of molecular formula C₉H₁₂OCl₂N₂ was isolated in 20% yield. The structure of the compound was established by degradation. In the case of acetyl chloride, N-isobutyryl-α-aminoisobutyroamide was obtained in 10% yield. The former is thought to have resulted from reaction of oxalyl chloride with the keteneimine, which is produced by combination of two 1-cyano-1-methylethyl radicals. The latter arises apparently from hydrolysis of the keteneimine during treatment. Benzoyl chloride did not undergo any reactions with 1-cyano-1-methylethyl radicals. The reaction mechanism is discussed.