米国産NTU頁岩油成分の研究(第3報) : AlkylpiperidineのHofmann分解

概要

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The Hofmann degradation of quaternary ammonium compounds was examined with 2-alkyl-, 2,4-dialkyl-, and 2,4,6-trialkyl-piperidinium iodides. Thermal decompotion of 2-pentylpiperidinium hydroxide (IV_6) produced 5-dimethylamino-1-decene (B) (47%), 1-dimethylamino-4-decene (C) (38%), and 1-dimethylamino-5-decene (D) (15%) (Table II). Elimination generally occurs preferentially in the piperidine ring, rather than in the 2-alkyl chain, except when the alkyl is a methyl group. This result may be interpreted as being due to the steric effect in the planer trans transition state during formation of olefins from quaternary bases.
公益社団法人日本薬学会の論文
1971-07-25