Spectroscopic and kinetic study of an intramolecular aromatic nucleophilic photosubstitution. Reaction mechanism of a photo-smiles rearrangement.
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概要
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Photo-Smiles rearrangement reaction of <I>N</I>-[ω-(<I>p</I>-nitrophenoxy)alkyl]aniline was studied by measuring the absorption spectra of transient species. Two intermediates <B>A</B> and <B>B</B> were observed and were assigned to a solvated ion pair and the Meisenheimer complex, respectively. The reaction scheme, starting material→intramolecular charge transfer on excitation→<B>A</B>→<B>B</B>→final product, was derived from the relative yields and lifetimes of <B>A</B> and <B>B</B> as well as from the effects of solvent polarity, of triethylamine and oxygen, and of the alkyl chain length on each step of reaction.
- 公益社団法人 日本化学会の論文
著者
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NAKAMURA Junko
The Institute of Physical and Chemical Research
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Mutai Kiyoshi
Department Of Chemistry Graduate School Of Arts And Sciences The University Of Tokyo
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Nagakura Saburo
The Institute for Solid State Physics The University of Tokyo
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Yokoyama Kenji
The Institute of Physical and Chemical Research
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Nakagaki Ryoichi
The Institute for Solid State Physics, The University of Tokyo
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Nakagaki Ryoichi
The Institute of Physical and Chemical Research
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Nagakura Saburo
The Institute for Molecular Science
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