Anthracene Photodimers. I. Elimination and Substitution Reactions of the Photodimer of 9-Bromoanthracene<sup>1</sup>

Applequist, Douglas E.; Litle, Robert L.; Friedrich, Edwin C.; Wall, Robert E.

doi:10.1021/ja01511a048

Cited by 31 publications

(6 citation statements)

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“…In contrast, anti-sesquinorbornene (24) potentially possesses a C2 axis of symmetry that lies along the C-C double bond. As a consequence of the equivalence of the two faces of the double bond, a planar equilibrium geometry at the doubly bonded carbons is at least a possibility for 24. syn-Sesquinorbornene ( 23) and derivatives were prepared by Paquette and co-workers37 during the course of a general study of long-range stereoelectronic control by norbornyl frameworks.38 Reaction of isodicyclopentadiene (25) with various dienophiles gave mainly adducts with the syn-sesquinorbornene skeleton. 39 The adduct with phenyl vinyl sulfone was converted to 23 by reduction with sodium amalgam.…”

Section: Sesqulnorbomenes and Related Alkenesmentioning

confidence: 99%

Pyramidalized alkenes

Borden¹

1989

Chem. Rev.

205

111

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Section: Sesqulnorbomenes and Related Alkenesmentioning

confidence: 99%

Pyramidalized alkenes

Borden¹

1989

Chem. Rev.

205

111

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“…However, the 1 H NMR spectra have revealed that only one product is present upon illumination in our case. According to the literature data, the dimer with trans located Br atoms (head-to-tail configuration) has been identified in previous studies [22,51]. Therefore, we assume that the resonances of a doublet at 7.76 ppm, a multiplet at 6.96 ppm and a singlet at 5.35 ppm belong to the head-to-tail isomer.…”

Section: Comparison Of a And B In Separate Samplesmentioning

confidence: 75%

“…Many studies have been devoted to the kinetics and reactivity of substituted anthracenes, which depends on the electronic properties of the substituent. Furthermore, different isomers of the dimer can be formed [9,22,23]. Therefore, the regio-and enantioselectivity of anthracene photodimerization has been investigated comprehensively, both via experiment and quantum chemistry calculations [24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

et al. 2021

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Anthracenes are an important class of acenes. They are being utilized more and more often in chemistry and materials sciences, due to their unique rigid molecular structure and photoreactivity. In particular, photodimerization can be harnessed for the fabrication of novel photoresponsive materials. Photodimerization between the same anthracenes have been investigated and utilized in various fields, while reactions between varying anthracenes have barely been investigated. Here, Nuclear Magnetic Resonance (NMR) spectroscopy is employed for the investigation of the photodimerization of two exemplary anthracenes: anthracene (A) and 9-bromoanthracene (B), in the solutions with only A or B, and in the mixture of A and B. Estimated k values, derived from the presented kinetic model, showed that the dimerization of A was 10 times faster in comparison with B when compounds were investigated in separate samples, and 2 times faster when compounds were prepared in the mixture. Notably, the photoreaction in the mixture, apart from AA and BB, additionally yielded a large amount of the AB mixdimer. Another important advantage of investigating a mixture with different anthracenes is the ability to estimate the relative reactivity for all the reactions under the same experimental conditions. This results in a better understanding of the photodimerization processes. Thus, the rational photofabrication of mix-anthracene-based materials can be facilitated, which is of crucial importance in the field of polymer and material sciences.

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“…Irradiation of a solution of 9-bromoanthracene 119 with visible light yields one regioisomer of the dimer 120 (Scheme 18). 90 This compound was successfully transformed into 9,9′,10,10′-tetradehydrodianthracene 121. 91 Photochemical reactions are frequently applied to the synthesis of such unusual, exotic hydrocarbon compounds.…”

Section: Photocycloadditions With Condensed Aromatic Compoundsmentioning

confidence: 99%

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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Anthracene Photodimers. I. Elimination and Substitution Reactions of the Photodimer of 9-Bromoanthracene¹

Cited by 31 publications

References 1 publication

Pyramidalized alkenes

Pyramidalized alkenes

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

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

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Anthracene Photodimers. I. Elimination and Substitution Reactions of the Photodimer of 9-Bromoanthracene1

Cited by 31 publications

References 1 publication

Pyramidalized alkenes

Pyramidalized alkenes

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

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

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Anthracene Photodimers. I. Elimination and Substitution Reactions of the Photodimer of 9-Bromoanthracene¹