New photochemical rearrangements and extrusion reactions of aromatic compounds induced by an intramolecular [2+2] photocycloaddition between a naphthalene and a resorcinol moiety

Hoffmann, Norbert

doi:10.1016/s0040-4020(02)00902-x

Cited by 15 publications

(13 citation statements)

References 74 publications

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“…80 Less symmetrical polyaromatics were also investigated, and substituted styrenes were shown to react regioselectively with chrysene (Scheme 31). 81 Hoffmann 82 reported intramolecular cycloaddition of resorcinol derivative 112, leading first to an ortho adduct 113, which then rearranges into naphthalene 114 in acidic medium (Scheme 32).…”

Section: Ortho Cycloaddition With Polycyclic Aromaticsmentioning

confidence: 99%

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: Ortho Cycloaddition With Polycyclic Aromaticsmentioning

confidence: 99%

Arene–Alkene Cycloaddition

2016

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“…In intramolecular photocycloadditions between the benzene ring and an alkene, often a competition between the [3 + 2] and [2 + 2] mode is observed. , Many of these reactions are reversible. In the case of phenol derivatives, these equilibria can be controlled by additives such as acid. − …”

Section: Introductionmentioning

confidence: 99%

Photocycloadditions of Arenes Derived from Lignin

et al. 2021

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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“…Acyl naphthalenes form an important class of chemicals with many applications such as substrates for the syntheses of peroxy-containing acetylenic alcohols and ethers [24], radicals initiator for polymerization [25], phototrigger inhibitors of termite survival [26], precursors for the preparation of some thiocarbonyl compounds that are important in chlorophyll a synthesis [27], and precursors for photocycloaddition studies of intramolecular rearrangements [28]. In this study, we have tested the SDFI strategy for ␣-and ␤-acyl naphthalenes, an important class of constitutional isomers.…”

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confidence: 99%

Absolute assignment of constitutional isomers via structurally diagnostic fragment ions: The challenging case of α- and β-acyl naphthalenes

Benassi

Eberlin

2010

J. Am. Soc. Mass Spectrom.

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A general mass spectrometric method is described for the absolute assignment of ␣-or ␤-acyl naphthalenes, via which the gaseous ␣-and ␤-naphthoyl cations of m/z 155 are used as structurally diagnostic fragment ions (SDFI). These stable acylium ions are common and normally abundant fragment ions of acylnaphthalenes in general. Using a pentaquadrupole mass spectrometer, CID experiments with argon and ion/molecule reactions with 2-methyl-1,3-dioxolane, isoprene, acetonitrile and propionitrile were performed but failed to distinguish the two SDFI. Reactions with ethyl vinyl ether and several homologues as well as ethyl vinyl thioether were, however, successful. In reactions with ethyl vinyl ether, the ␣-SDFI form a pair of diagnostic product ions of m/z 165 and m/z 181, which are absent in the corresponding spectrum of the ␤-SDFI. Methyl 4-(1-naphthyl)-2,4-dioxobutanoate was used as a test molecule for this class of constitutional isomers and absolute structural assignment as an ␣-acyl naphthalene was correctly performed via the characterization of its ␣-SDFI. (J Am Soc Mass Spectrom

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New photochemical rearrangements and extrusion reactions of aromatic compounds induced by an intramolecular [2+2] photocycloaddition between a naphthalene and a resorcinol moiety

Cited by 15 publications

References 74 publications

Arene–Alkene Cycloaddition

Arene–Alkene Cycloaddition

Photocycloadditions of Arenes Derived from Lignin

Absolute assignment of constitutional isomers via structurally diagnostic fragment ions: The challenging case of α- and β-acyl naphthalenes

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