16304-93-1Relevant academic research and scientific papers
Azulenophenanthrenes from 2,2′-Di(arylethynyl)biphenyls through C-C bond cleavage of a benzene ring
Matsuda, Takanori,Goya, Tsuyoshi,Liu, Lantao,Sakurai, Yusuke,Watanuki, Shoichi,Ishida, Naoki,Murakami, Masahiro
, p. 6492 - 6495 (2013/07/19)
From six to seven: 2,2′-Di(arylethynyl)biphenyls undergo a skeletal rearrangement in the presence of a platinum(II) catalyst to afford polycyclic aromatic compounds containing an azulene unit. The reaction involves C-C bond cleavage of a benzene ring, which expands into a seven-membered ring. Copyright
Revisit of the dessy-white intramolecular acetylene-acetylene [2 + 2] cycloadditions
Lee, Chung-Chieh,Leung, Man-Kit,Lee, Gene-Hsiang,Liu, Yi-Hung,Peng, Shie-Ming
, p. 8417 - 8423 (2007/10/03)
In this experiment, a series of thermal reactions of 4,4′- disubstituted 2,2′-bis(phenylethynyl)biphenyls with 2,3,4,5- tetraphenylcyclopenta-2,4-dienone were carried out under neat conditions and in diphenyl ether at temperatures between 260 and 270 °C t
Tellurium-Mediated Halogen Transer from Polyhaloalkanes to Diyne Acceptors
Blum, Jochanan,Baidossi, Wael,Badriech, Yacoub,Hoffman, Roy E.,Schumann, Herbert
, p. 4738 - 4742 (2007/10/02)
Elemental tellurium catalyzes transfer of halogen from (CHCl2)2, from C2HCl5 and from (CHBr2)2, to the phenylated diynes 1-3, 17, 20, and 24, in which the alkyne moieties are in close proximity.The process is associated with cyclorearrangement reactions by which halogenated polycycles are formed.In boiling C2HCl5, derivatives of 1,2-bis(phenylethynyl)benzenes afford 5-halogenated indenoindenes, 1,8-bis(phenylethynyl)naphthalene gives a chlorinated benzofluoranthene derivative, and 2,2'-bis(phenylethynyl) forms 9-chloro-14-phenylbenzanthracene.Diynes 25 and 26 in which the ethynyl functions are further removed from each other fail to yield halogenated products.Diyne 25 undergoes oxidative cyclization by which 1,3-diphenyldibenzocycloheptafuran (29) is formed.Compound 26 is transformed to hydrocarbon 32, which involves a phenyl ring walk and elimination of H2Te.
Anomaly in Palladium-Catalyzed Phenylethynylation of 2,2'-Dihalobiphenyls: Formation of Alkylidenefluorenes
Dougherty, T. Kirk,Lau, Kreisler S. Y.,Hedberg, Frederick L.
, p. 5273 - 5280 (2007/10/02)
2,2'-Diiodobiphenyl and 5,5'-dinitro-2,2'-dihalobiphenyls underwent palladium-catalyzed phenylethynylation with 2 mol of phenylacetylene to yield 3-(fluoren-9-ylidene)-1,3-diphenylpropyne and 3-(3,6-dinitrofluoren-9-ylidene)-1,3-diphenylpropyne, respectively.These fluorenyl compounds exhibited well-defined splitting patterns for the fluorenyl ring protons in the 250-MHz proton NMR spectra.The structure of 3-(fluoren-9-ylidene)-1,3-diphenylpropyne was further confirmed by an independent synthesis via the thermolysis of diethyl 3-(fluoren-9-ylidene)-1,3-diphenylpropen-1-yl phosphate.The mechanistic importance of the complex iodo(fluoren-9-ylidenebenzyl)bis(triphenylphosphine)palladium(II) in the catalytic cycle was established on the basis of its reaction with phenylacetylene to give 3-(fluoren-9-ylidene)-1,3-diphenylpropyne.
