Kinetic studies on the N,N-type smiles rearrangement.
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概要
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The Smiles rearrangement reaction of DL-2-aminododecanoic acid <I>N</I>-methyl-<I>p</I>-nitroanilide to DL-2-(<I>p</I>-nitrophenyl)aminododecanoic acid <I>N</I>-methylamide has been investigated in aqueous alkaline media containing 0–50% (v/v) acetonitrile or ethanol at 25 °C. It was found from the pH-rate profile that the reactive species is the free base form of the substrate. Acetonitrile content in the medium appreciably affected the rate with a maximum at <I>ca.</I> 20% in the acetonitrile content. The cationic CTAB micelles accelerated the rate 4.4-fold at pH 10, while the anionic SDS micelles suppressed the reaction almost completely. These effects of solvent and micelles were qualitatively correlated with the transition state of the reaction. A plausible mechanism for this reaction is the Smiles type rearrangement in which a spiro σ-complex is involved. The activation parameters obtained and suppression of the reaction rate by Cu(II) ion are in line with the proposed reaction mechanism.
- 公益社団法人 日本化学会の論文
著者
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Kondo Hiroki
Deparment Of Physics Saga University
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Okamoto Hiroshi
Department Of Advanced Biological Sciences For Regeneration (kotobiken Medical Laboratories) Tohoku
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SUNAMOTO JUNZO
Department of Applied Chemistry and Biotechnology, Niihama National College of Technology
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Yanase Fumihiro
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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