The Glow-discharge Reactions of Pyrrole, Pyrrolidine, and Butylamine

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Abstract
The glow-discharge reactions of pyrrole, pyrrolidine, and butylamine were carried out. Pyrrolidine produces a complex mixture of products, the most prevalent of which is (Remark: Graphics omitted.) (R: H, CH3, and C2H5), and butylamine yielded primarily CH3(CH2)3N=CHR (R: CH3, C2H5, and C3H7) along with CH3(CH2)3NHCH2CN, whereas pyrrole afforded a mixture of acrylonitrile, crotononitrile, benzene, α-methylpyrrole and β-methylpyrrole, together with large amounts of HCN. The formation of characteristic products, α-(1-pyrrolidinyl) nitrile derivatives with pyrrolidine, and the yield of butylaminoacetonitrile with butylamine can be explained by considering the formation of a resonance-stabilized α-cyanoalkyl radical as the most probable intermediate which attacks a nitrogen atom of pyrrolidine and that of butylamine or which recombines with pyrrolidine-N-radical and butylamine-N-radical.