213-46-7Relevant articles and documents
Geissmann et al.
, p. 793 (1967)
Hayward,Leznoff
, p. 5115,5119 (1971)
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Ruzicka,Hoesli
, p. 470,473 (1934)
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Preparation of (substituted) picenes via solar light-induced Mallory photocyclization
Protti, Stefano,Artioli, Gianluca A.,Capitani, Francesco,Marini, Carlo,Dore, Paolo,Postorino, Paolo,Malavasi, Lorenzo,Fagnoni, Maurizio
, p. 27470 - 27475 (2015)
Picenes 2a-c were readily obtained via photocyclization of dinaphthylethenes 1a-c by a straightforward solar light-induced Mallory reaction. The product was easily recovered by simple filtration after exposure of the reaction mixture to sunlight. The polyene obtained was then characterized by means of Raman spectroscopy and X-ray diffraction.
Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons
Zhao, Zhensheng,Britt, Liam H.,Murphy, Graham K.
, p. 17002 - 17005 (2018/11/01)
A catalytic, metal-free and chemoselective oxidative intramolecular coupling of arene and alkene C?H bonds is reported. The active hypervalent iodine (HVI) reagent, generated catalytically in situ from iodotoluene and meta-chloroperoxybenzoic acid (m-CPBA), reacts with o-vinylbiphenyls to generate polyaromatic hydrocarbons in up to 95 % yield. Experimental evidence suggests the reactions proceed though vinyliodonium and, possibly, vinylenephenonium intermediates.
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.
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
supporting information, p. 2960 - 2963 (2017/03/11)
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.
