Lithium-Diphenyl錯体によるPiperidinium塩類の還元的環開裂反応

抄録

Piperidinium iodide and some alkyl-substituted piperidinium iodides were treated with lithium-diphenyl adduct in anhydrous tetrahydrofuran in order to study the possible reductive cleavage reaction of the piperidine ring. 1, 1-Dimethyl-2-nonylpiperidinium iodide (I₄) was found to undego reductive ring cleavage and yield 5-(N, N-dimethylamino)-tetradecane (2%) and N, N-dimethyltetradecylamine (36%), together with N-methyl-2-nonylpiperidine (21%) and 1-dimethylamino-5-tetradecene (36%). In the reaction of I₄ with lithium aromatic hydrocarbons, the ease of reductive ring cleavage increased with decrease in the electron affinity of the hydrocarbons.