Kinetics and mechanism of thermal isomerisation of aryl alkanehydrazonates into N',N'-diarylhydrazides. Extension of a recent free radical analogue of the chapman rearrangement.
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概要
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A series of twelve aryl <I>N</I>-(<I>p</I>-nitrophenyl)alkanehydrazonates (I) have been prepared and their thermal rearrangement into <I>N</I>-acyl-<I>N</I>′,<I>N</I>′-diarylhydrazines (II) was investigated. The structures of I and II were derived from their elemental analyses and spectral properties. Hydrolysis of II afforded the corresponding <I>N</I>′,<I>N</I>′-diarylhydrazines. Kinetic experiments have shown that electron withdrawing substituents decrease the rate of the rearrangement whereas electron donating groups increase it. The rate of conversion of I into II was also increased by addition of benzoyl peroxide. A free radical mechanism was proposed to account for the results.
- 公益社団法人 日本化学会の論文
著者
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Almousawi Saleh
Department of Chemistry, Faculty of Science, University of Cairo
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Shawali Ahmad
Department of Chemistry, Faculty of Science, University of Cairo
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Hassaneen Hamdi
Department of Chemistry, Faculty of Science, University of Cairo
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- Kinetics and mechanism of thermal isomerisation of aryl alkanehydrazonates into N',N'-diarylhydrazides. Extension of a recent free radical analogue of the chapman rearrangement.