3351-28-8Relevant academic research and scientific papers
Convenient Phenacene Synthesis by Sequentially Performed Wittig Reaction and Mallory Photocyclization Using Continuous-Flow Techniques
Okamoto, Hideki,Takahashi, Haruhiko,Takane, Takamitsu,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi,Gohda, Shin,Yamaji, Minoru
, p. 2949 - 2957 (2017/06/27)
Various phenacenes possessing chrysene, picene, and fulminene frameworks were prepared by using a continuous-flow synthetic protocol in which Wittig reaction affording diarylethenes and their Mallory photocyclization producing phenacene skeletons were sequentially performed. The Wittig reaction solution, containing the diaryl ethene obtained from an arylaldehyde and an arylmethyltriphenylphosphonium salt, was mixed with an iodine solution in the flow system and, subsequently, the solution was subjected to the photoreaction. Desired phenacenes were obtained with high to moderate chemical yield. For the present protocol, isolation of the intermediary diarylethene, which is the key precursor of the phenacene, is unnecessary. The approach provides a convenient method to supply a variety of phenacene samples, which are needed for initial systematic surveys in material science.
3,3′,5,5′-Tetra- tert -butyl-4,4′-diphenoquinone (DPQ)-Air as a New Organic Photocatalytic System: Use in the Oxidative Photocyclization of Stilbenes to Phenacenes
Carrera, Manuel,De La Viuda, Mónica,Guijarro, Albert
supporting information, p. 2783 - 2787 (2016/12/16)
We report an organic photocatalytic system, namely 3,3′,5,5′-tetra-tert-butyl-4,4′-diphenoquinone (DPQ) and air, capable of coupling efficiently with the photocyclization of stilbenes to afford phenacenes. The potential of this new and mild process is shown with the synthesis of [5]- and [7]phenacene, two semiconductors recently implemented into organic electronic devices, with high yields and remarkable purity.
Efficient synthetic photocyclization for phenacenes using a continuous flow reactor
Okamoto, Hideki,Takane, Takamitsu,Gohda, Shin,Kubozono, Yoshihiro,Sato, Kaori,Yamaji, Minoru,Satake, Kyosuke
, p. 994 - 996 (2014/07/22)
The continuous flow reaction technique has been applied to the photocyclization of 1,2-diarylethenes, the so-called Mallory reaction, to afford phenacenes in high chemical yields and efficiencies (114-288mg h-1). The present technique will allow us to produce several grams of phenacenes at a time.
Palladium-catalyzed intramolecular C-H activation: A synthetic approach towards polycyclic aromatic hydrocarbons
Paul, Sunanda,Jana, Rathin,Ray, Jayanta K.
experimental part, p. 1463 - 1468 (2010/08/20)
A simple and convenient synthetic protocol for the construction of polycyclic aromatic hydrocarbons has been developed. A variety of phenanthrene, benzo[c]phenanthrene and chrysene derivatives was synthesized via Pd-catalyzed intramolecular C-H activation followed by acid-catalyzed water elimination.
