A rationalization of orientation in nucleophilic aromatic photosubstitution.
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概要
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Consideration of the relationship between the mechanisms and orientation effects of the nitro group in nucleophilic photosubstitutions of nitroaromatics leads to the proposal of two rules, making use of frontier molecular orbital theory, for interpreting the regioselectivities and determining the reaction mechanisms. The first rule is a summary of previously proposed interpretations, concerning photoreactions accompanying the direct addition of a nucleophile to an excited nitroaromatic substrate. In this case, the regioselectivity is governed by the HOMO of the substrate. The second rule regards reactions involving photo-induced electron transfer, where regioselectivity is LUMO-controlled. The application of these rules is successfully demonstrated for various types of compounds.
- 公益社団法人 日本化学会の論文
著者
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NAKAGAKI Ryoichi
Institute for Molecular Science
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Mutai Kiyoshi
Department Of Chemistry Graduate School Of Arts And Sciences The University Of Tokyo
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Tukada Hideyuki
Department of Chemistry, College of Arts and Sciences, The University of Tokyo Komaba
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