One‐Step Synthesis of Benzotetra‐ and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene

Mukae, Hirofumi; Maeda, Hideaki; Mizuno, Kazuhiko

doi:10.1002/ange.200602553

Cited by 10 publications

(4 citation statements)

References 35 publications

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“…176 The more complex structures 367 were obtained in good yields (74% and 85% respectively). Also, reaction with an oxygen within the tether gave moderate to excellent yields of the meta adduct (up to 84%); however, for 364, 29% of the ortho adduct was also observed.…”

Section: Meta Cycloaddition With Naphthalene Derivativesmentioning

confidence: 96%

Arene–Alkene Cycloaddition

2016

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Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of view, both olefinic and diene subunits; however, the stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical activation opens interesting perspectives, as one can selectively provide excess energy to one of the reactants but not to the product, thus preventing thermal back reaction. Indeed, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.

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Section: Meta Cycloaddition With Naphthalene Derivativesmentioning

confidence: 96%

Arene–Alkene Cycloaddition

2016

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“…Reversibility of intramolecular [2+2]-photocycloadditions of double bonds to the 1-cyanonaphthalene system, preceding the [3+2]-photocycloaddition, have also been observed by Mizuno et al 22,23 The course of the observed photocycloadditions Monochromatic (313 nm) excitation of a common equimolar solution of 1 and model compound 2 in acetonitrile had shown a marked decrease of the absorbance between 250 and 290 nm and no isosbestic points over the wavelength range 240-380 nm in the reaction spectrum, demonstrating that only products of lower absorbance than that of either starting material are produced. The graphical evaluation of the reaction spectrum gave linear absorbancy-time and absorbancy diagrams 43 .…”

Section: Methodsmentioning

confidence: 63%

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Döpp¹,

Kruse²,

Erian³

et al. 2013

Arkivoc

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2-(Cycloamino)propenenitriles H 2 C=C(CN)N(CH 2 ) n (n = 4, 5, 6, 7) are added to triplet π,π*-excited 1-acetonaphthone forming 8b-acetyl-2-(cycloamino)-1,2,2a,8b-tetrahydrocyclobuta-[a]naphthalene-2-carbonitriles as well as 1-acetyl-9-(cycloamino)-1,4-dihydro-1,4-ethanonaphthalene-9-carbonitriles. Regio-and stereoselectivity of the photocycloadditions and the special role of the cyclobuta[a]naphthalene adducts in the initial stage of the photoadditions are discussed.

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“…Thus the UV irradiation of the 1-cyanonaphthalene derivatives 91 efficiently yielded the [2 + 3] cycloadducts 92 (Scheme 13). 77 These results have been obtained after prolonged irradiation. Short time irradiation efficiently leads to cycloadducts such as 93.…”

Section: Photocycloadditions With Condensed Aromatic Compoundsmentioning

confidence: 83%

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

Hoffmann

2012

Photochem Photobiol Sci

124

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Electronic excitation significantly changes the reactivity of chemical compounds. Compared to ground state reactions, photochemical reactions considerably enlarge the application spectrum of a particular functional group in organic synthesis. Multistep syntheses may be simplified and perspectives for target oriented synthesis (TOS) and diversity oriented synthesis (DOS) are developed. New compound families become available or may be obtained more easily. In contrast to common chemical reagents, photons don't generate side products resulting from the transformation of a chemical reagent. Therefore, they are considered as a traceless reagent. Consequently, photochemical reactions play a central role in the methodology of sustainable chemistry. This aspect has been recognized since the beginning of the 20th century. As with many other photochemical transformations, photochemical reactions of aromatic, benzene-like compounds illustrate well the advantages in this context. Photochemical cycloadditions of aromatic compounds have been investigated for a long time. Currently, they are applied in various fields of organic synthesis. They are also studied in supramolecular structures. The phenomena of reactivity and stereoselectivity are investigated. During recent years, photochemical electron transfer mediated reactions are particularly focused. Such transformations have likewise been performed with aromatic compounds. Reactivity and selectivity as well as application to organic synthesis are studied.

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One‐Step Synthesis of Benzotetra‐ and Benzopentacyclic Compounds through Intramolecular [2+3] Photocycloaddition of Alkenes to Naphthalene

Cited by 10 publications

References 35 publications

Arene–Alkene Cycloaddition

Arene–Alkene Cycloaddition

Photocycloaddition of four homologous 2-(cycloamino)propenenitriles to 1-acetonaphthone

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent

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