Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 

Saved Queries

Sign in to use this feature.

Search Filter Reset All

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Subjects Reset
Select Subjects

Journals

remove_circle_outline
remove_circle_outline
Add Journals Reset
Select Journals

Article Types

remove_circle_outline
remove_circle_outline
Add Article Types Reset
Select Article Types

Countries / Regions

remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Countries / Regions Reset
Select Countries / Regions
Update Search
share announcement

Search Results (4)

Search Parameters:
Keywords = Mallory reaction

Order results
Result details
Results per page
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
13 pages, 1503 KiB  
Article
Regiospecific Photochemical Synthesis of Methylchrysenes
by Thomas Böhme, Mari Egeland, Marianne Lorentzen, Mohamed F. Mady, Michelle F. Solbakk, Krister S. Sæbø and Kåre B. Jørgensen
Molecules 2023, 28(1), 237; https://doi.org/10.3390/molecules28010237 - 28 Dec 2022
Cited by 2 | Viewed by 2125
Abstract
Methylated polycyclic aromatic hydrocarbons (PAHs) are suspected to be some of the toxic compounds in crude oil towards marine life and are needed as single compounds for environmental studies. 1-, 3- and 6-methylchrysene (3a,b,c) were prepared as single isomers by photochemical [...] Read more.
Methylated polycyclic aromatic hydrocarbons (PAHs) are suspected to be some of the toxic compounds in crude oil towards marine life and are needed as single compounds for environmental studies. 1-, 3- and 6-methylchrysene (3a,b,c) were prepared as single isomers by photochemical cyclization of the corresponding stilbenoids in the Mallory reaction using stoichiometric amounts of iodine in 82-88% yield. 2-methylchrysene (3d) was prepared by photochemical cyclization where the regioselectivity was controlled by elimination of an ortho-methoxy group under acidic oxygen free conditions in 72% yield. These conditions failed to form 4-methylchrysene from the corresponding stilbenoid. All stilbenoids were made from a common naphthyl Wittig salt and suitably substituted benzaldehydes. We have also demonstrated that methylchrysenes can be oxidized to the corresponding chrysenecarboxylic acids by KMnO4 in modest yields. Full article
(This article belongs to the Section Photochemistry)
►▼ Show Figures

Graphical abstract

18 pages, 2562 KiB  
Article
Synthesis, Stereochemical and Photophysical Properties of Functionalized Thiahelicenes
by Valentina Pelliccioli, Francesca Cardano, Giacomo Renno, Francesca Vasile, Claudia Graiff, Giuseppe Mazzeo, Andrea Fin, Giovanna Longhi, Sergio Abbate, Alessia Rosetti, Claudio Villani, Guido Viscardi, Emanuela Licandro and Silvia Cauteruccio
Catalysts 2022, 12(4), 366; https://doi.org/10.3390/catal12040366 - 23 Mar 2022
Cited by 7 | Viewed by 3723
Abstract
We report on the synthesis of a novel class of functionalized thia[6]helicenes and a thia[5]helicene, containing a benzothiophene unit and a second heteroatom embedded in the helix (i.e., nitrogen and oxygen) or a pyrene or a spirobifluorene moiety. These systems are obtained through [...] Read more.
We report on the synthesis of a novel class of functionalized thia[6]helicenes and a thia[5]helicene, containing a benzothiophene unit and a second heteroatom embedded in the helix (i.e., nitrogen and oxygen) or a pyrene or a spirobifluorene moiety. These systems are obtained through straightforward and general procedures that involve: (i) palladium-catalyzed annulation of iodo-atropoisomers with internal alkynes and (ii) Suzuki coupling of iodo-atropoisomers with phenyl boronic acid followed by a Mallory-type reaction. Both experimental and theoretical studies on the configurational stability of some selected thia[6]helicenes confirmed their stability toward racemization at room temperature, while the pyrene-based thia[5]helicene was found to be unstable. Moreover, the configuration assignment for one representative thiahelicene was established through the comparison between experimental and theoretical circular dichroism (CD) spectra. A systematic study of the photophysical properties of both thiahelicenes and the corresponding atropoisomers has been carried out to provide a complete overview on the new molecules proposed in this work. The obtained data showed regular trends in all the thiahelicene series with spectroscopic traits in line with those previously observed for similar heterohelicenes. Full article
(This article belongs to the Special Issue Catalysts for the Synthesis of Heterocyclic Compounds)
►▼ Show Figures

Figure 1

10 pages, 2442 KiB  
Article
Fluorine-Containing Dibenzoanthracene and Benzoperylene-Type Polycyclic Aromatic Hydrocarbons: Synthesis, Structure, and Basic Chemical Properties
by Otohiro Gotsu, Tomomi Shiota, Hiroki Fukumoto, Tomoko Kawasaki-Takasuka, Takashi Yamazaki, Tomoko Yajima, Tomohiro Agou and Toshio Kubota
Molecules 2018, 23(12), 3337; https://doi.org/10.3390/molecules23123337 - 16 Dec 2018
Cited by 7 | Viewed by 6205
Abstract
Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs). In this study, dibenzoanthracene-type (4a) and benzoperylene-type ( [...] Read more.
Intramolecular photocyclization of stilbene derivatives (Mallory reaction) is one of the efficient methods for building polycyclic aromatic hydrocarbon (PAH) frameworks, and is also expected to be applicable to synthesis of fluorine-containing PAHs (F-PAHs). In this study, dibenzoanthracene-type (4a) and benzoperylene-type (4b) F-PAHs were synthesized using the Mallory reaction of the 1,4-distyrylbenzene-type π-conjugated molecule (3a), which was prepared by addition-defluorination of available octafluorocyclopentene (OFCP) and aryllithium in three steps. The structure of 4a originating from π–π interaction was characterized by X-ray crystallographic analysis. The absorption maxima of UV-Vis spectra and emission maxima of photoluminescence spectra of the PAHs were positioned at a longer wavelength compared to those of the corresponding unsubstituted PAHs, presumably due to the electron-withdrawing nature of perfluorocyclopentene (PFCP) units. The effect of PFCP units in F-PAHs was also studied by time-dependent density functional theory (TD-DFT) calculation. Full article
(This article belongs to the Special Issue Polycyclic Aromatic Hydrocarbons: Synthesis, Characterisation and Application)
►▼ Show Figures

Graphical abstract

25 pages, 294 KiB  
Review
Photochemical Oxidative Cyclisation of Stilbenes and Stilbenoids—The Mallory-Reaction
by Kåre B. Jørgensen
Molecules 2010, 15(6), 4334-4358; https://doi.org/10.3390/molecules15064334 - 14 Jun 2010
Cited by 228 | Viewed by 18936
Abstract
After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of [...] Read more.
After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of the reaction was reviewed by Mallory in 1984in a huge chapter in the Organic Reactions series, but the development has continued. Alternative conditions accommodate more sensitive substituents, and isomers can be favoured by sacrificial substituents. Herein the further developments and applications of this reaction after 1984 are discussed and summarized. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying article 1-50 on page 1 of 1.
Back to TopTop