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.
Production of [pisen[pisen] and derivatives thereof
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Paragraph 0040, (2017/07/07)
PROBLEM TO BE SOLVED: To provide a method of producing a picene and a derivative thereof suitable for uses of organic semiconductors, thin film transistors, field effect transistors or solar batteries or the like, in a short reaction process with high yield.SOLUTION: A method of producing a picene of formula 8 and a derivative thereof includes, as represented compounds and steps, a step 1 to subject a compound of formula 5 and a compound of formula 6 to a coupling reaction for producing a compound of formula 7, and a step 2 to subject the compound of formula 7 to dehydrohalogenation.
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
, 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.