17580-25-5Relevant academic research and scientific papers
Alumina-Mediated π-Activation of Alkynes
Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Sharapa, Dmitry I.
supporting information, p. 15420 - 15426 (2021/09/30)
The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.
Palladium-catalyzed synthesis of 7,9-diaryl-8 H-acenaphtho[1,2-c]pyrroles and their application in explosives detection
Chen, Xiaopeng,Jin, Jisong,Wang, Yanguang,Lu, Ping
scheme or table, p. 9920 - 9923 (2011/10/09)
Making sensors of pyrroles: 7,9-Diarenyl-8H-acenaphtho[1,2-c]pyrroles were efficiently constructed by a palladium-catalyzed bicyclization of 1,8-diarenynyl naphthalenes and primary amines under air conditions (see scheme). The synthesized 8H-acenaphtho[1,
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.
ON THE VARIOUS MODES OF INTERACTION OF SULFUR WITH PHENYLATED DIYNES
Blum, Jochanan,Badrieh, Yacoub,Shaaya, Osnat,Meltser, Larisa,Schumann, Herbert
, p. 87 - 96 (2007/10/02)
The reaction of elemental sulfur and five diynes of general formula PhCC(G)nCCR has been studied.While 1-(1-propynyl)-2-phenylethynylbenzene 1b reacted at 120 deg C to give solely 6-methylbenzindenothiopyran 2b, 1,1'-(1,2-phenylene)bis(3-phenyl-2-propyn-1-one) 4 and 1,8-bis(phenylethynyl)naphthalene 5 yielded the sulfides 11,11'-thiobis-(6-phenyl-5,12-naphthacenedione) 9 and 12,12'-thiobis(7-phenylbenzo-fluoranthene) 13, respectively, as the major products.Diyne 5 gave also a small amount of bis(7-phenylbenzofluoranthene-12-yl)disulfide 14. 3,3'-Oxybis(1-phenyl-1-propyne) 6 did not react in the absence of a metallic additive, but yielded 4,6-diphenyl-1H,3H-thienofuran 15 in the presence of equimolar quantities of RhCl3*3H2O and Aliquat-336.The reaction of the conjugated diyne 1,1'-(1,3-butadiyne-1,4-diyl)bisbenzene 7 with sulfur afforded 3,6-diphenyldithiolo-1,2-dithiole 16. Key words: Sulfur addition to diynes; benzindenothiopyran; dithiolo-1,2-dithiole; polycyclic sulfides; polycyclic disulfides.
The Photoelectrochemical Oxidation of Bis(benzylidene)acenaphthene
Compton, Richard G.,Fisher, Adrian C.,Wellington, Robert G.,Winkler, Jacob,Bethell, Donald,Lederer, Pavel
, p. 1359 - 1362 (2007/10/02)
The oxidation of bis(benzylidene)acenaphthene in acetonitrile solution at platinum electrodes irradiated with light (377 nm) has been investigated using a combination of channel electrode and spectrofluorimetric voltammetries.The efficient formation of the highly fluorescent molecule 7-phenylbenzofluoranthene was demonstrated and the electrode reaction mechanism characterised as of the 'photo-CE' type.Kinetic parameters relating to this process are reported.
Spectrofluorimetric Hydrodynamic Voltammetry: Theory and Practice
Compton, R. G.,Fisher, A. C.,Wellington, R. G.,Winkler, J.
, p. 8153 - 8157 (2007/10/02)
A flow cell for simultaneous spectrofluorimetric voltammetry is described.The relevant theory is presented and the sensitivity of the technique evaluated.Experiments involving (a) the photooxidation of bis(benzylidene)acenaphthene and (b) the oxidation of p-phenylenediamine are shown to be in good agreement with theory.It is demonstrated that the technique can reveal the existence of trace quantities of electrode reaction intermediates and products and show previously unsuspected species participating in the electrode process.
