Journal ArticleDOI
Photoinduoed molecular transformations. Part 146. Photoacylation and photoalkylation of 2-arylamino- and 2-alkylamino-1,4-naphthoquinones
Kazuhiro Kobayashi,Masayoshi Suzuki,H. Takeuchi,Atsushi Konishi,Hideo Sakurai,Hiroshi Suginome +5 more
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TLDR
The photoacylation of 2-arylamino- or 2-alkyl-2-anilino-1,4-naphthoquinones with aromatic or aliphatic aldehydes can be achieved in high yields when a solution of N-substituted 2-amino and an aldehyde in benzene is irradiated in the presence of benzophenone as discussed by the authors.Abstract:
The photoacylation of 2-arylamino- or 2-alkylamino-1,4-naphthoquinones with aromatic or aliphatic aldehydes can be achieved in high yields when a solution of N-substituted 2-amino-1,4-naphthoquinones and an aldehyde in benzene is irradiated in the presence of benzophenone. Irradiation of 2-anilino-1,4-naphthoquinones and cyclic ethers, such as tetrahydrofuran or dioxane, in the presence of benzophenone led to analogous photoalkylation products, 3-alkyl-2-anilino-1,4-naphthoquinones, in high yield. 1,4-Dihydroxy-2-diphenylamino-3-propionylnaphthalene, characterized as the diacetate, could be isolated from the photoacylation of 2-diphenylamino-1,4-naphthoquinones with propanal. The photoacylation thus involves hydroquinone derivatives as intermediates. Radical processes involving the formation of acyl or alkyl radicals from aldehydes or cyclic ethers by hydrogen abstraction with excited benzophenone for these photoacylations and photoalkylations are proposed.read more
Citations
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Photocatalysis for the formation of the C-C bond.
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Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes.
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Metal-Free CH Bond Activation of Branched Aldehydes with a Hypervalent Iodine(III) Catalyst under Visible-Light Photolysis: Successful Trapping with Electron-Deficient Olefins
TL;DR: Use of a hypervalent iodine(III) catalyst under visible light photolysis allows a mild way of generating acyl radicals from various branched aldehydes, thereby giving the corresponding hydroacylated products almost exclusively.
Journal ArticleDOI
Cerium salts in the oxidative free radical reactions between 2-amino-1,4-naphthoquinones and β-dicarbonyl compounds
TL;DR: The oxidative free radical reactions between 2-amino-1,4-naphthoquinones and β-dicarbonyl compounds mediated by cerium(IV) salts are described and provide a novel method for the synthesis of benzo[f]indole-4,9-diones exclusively.
Journal ArticleDOI
Solvent effects on the oxidative free radical reactions of 2-amino-1,4-naphthoquinones
TL;DR: In this article, the manganese (III) initiated oxidative free radical reactions of 2-amino-1,4-naphthoquinones are described and the free radical reaction provides a novel method for the synthesis of benzo[f]indole-4,9-diones.
References
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Mechanisms of Photochemical Reactions in Solution. XXXIII. Intersystem Crossing Efficiencies
TL;DR: In this article, a simple method for measurement of quantum yields for the singlet→triplet crossing process in solution has been developed, where the compound to be tested is used as a sensitizer for one or more cis-trans isomerization reactions and the quantum yield of the induced process is measured.
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Electronic spectra of substituted naphthoquinones
TL;DR: In this paper, the electronic spectra of substituted naphthoquinones were examined and a number of empirical correlations were derived that are useful in the structure determination of unknown pigments.
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Synthetic applications of the photochemically induced addition of oxycarbinyl species to α-enones. Part II. The addition of ketals, aldehydes, and polyfunctional species
TL;DR: In this paper, photochemically induced conjugate addition to a variety of α-enones to give 1, 4-ketols, 1,4-keto ketols, and 1 4-diketones is described.
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The Very Weak Visible Absorption Band of p-Benzoquinone
TL;DR: In this article, the very weak absorption bands at the long wavelength sides of the n→π* singlet-singlet absorption bands of p-benzoquinone and its derivatives were examined with regard to the solvent effect, the substitution effect and the temperature dependency.