146276-26-8Relevant articles and documents
Addition and cyclization reactions in the thermal conversion of hydrocarbons with an enyne structure, 4: Formation and rearrangements of bicyclic C10H8 aromatics from 1-phenyl-1-buten-3-yne
Schulz, Kathrin,Hofmann, Joerg,Zimmermann, Gerhard
, p. 2535 - 2539 (1997)
The thermal conversion of 1-phenyl-1-buten-3-yne (1) into the cycloisomerization products naphthalene (2), azulene (3), and 1-methylene-1H-indene (4) has been studied at temperatures between 550 and 1000°C, a reaction time of approximately 0.3 s at 13 Tor
Synthesis of bis(alk-3-en-1-ynyl)benzene with either E- or Z-configuration via a one-pot three-component coupling reaction and its optical properties
Hoshi, Masayuki,Suzuki, Souichi,Saitoh, Shingo,Okimoto, Mitsuhiro,Shirakawa, Kazuya
, p. 119 - 124 (2007)
A convenient, efficient and stereoselective synthesis of a range of bis(alk-3-en-1-ynyl)benzenes with E- and Z-configuration is described. The protocol involves Cu-mediated cross-coupling reaction of (E)- and (Z)-alk-1-enyldisiamylboranes with (trimethyls
Double cycloaromatization of (Z,Z)-deca-3,7-diene-1,5,9-triyne: Evidence for the intermediacy and diradical character of 2,6-didehydronaphthalene
Bharucha, Kamal N.,Marsh, Rebecca M.,Minto, Robert E.,Bergman, Robert G.
, p. 3120 - 3121 (1992)
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Probing E/Z isomerization on the C10H8 potential energy surface with ultraviolet population transfer spectroscopy
Newby, Josh J.,Mueller, Christian W.,Liu, Ching-Ping,Zwier, Timothy S.
, p. 1611 - 1620 (2010)
The excited-state dynamics of phenylvinylacetylene (1-phenyl-1-buten-3-yne, PVA) have been studied using laser-induced fluorescence spectroscopy, ultraviolet depletion spectroscopy, and the newly developed method of ultraviolet population transfer spectroscopy. Both isomers of PVA (E and Z) show a substantial loss in fluorescence intensity as a function of excitation energy. This loss in fluorescence was shown to be due to the turn-on of a nonradiative process by comparison of the laser-induced fluorescence spectrum to the ultraviolet depletion spectrum of each isomer, with a threshold 600 cm -1 above the electronic origin in Z-PVA and 1000 cm-1 above the electronic origin in E-PVA. Ab initio and density functional theory calculations have been used to show that the most likely source of the nonradiative process is from the interaction of the ππ* state with a close lying πσ* state whose minimum energy structure is bent along the terminal CCH group. Ultraviolet population transfer spectroscopy has been used to probe the extent to which excited-state isomerization is facilitated by the interaction with the πσ* state. In ultraviolet population transfer spectroscopy, each isomer was selectively excited to vibronic levels in the S1 state with energies above and below the threshold for fluorescence quenching. The ultraviolet-excited populations are then recooled to the zero point levels using a reaction tube designed to constrain the supersonic expansion and increase the collision cooling capacity of the expansion. The new isomeric distribution was detected in a downstream position using resonant-2-photon ionization spectroscopy. From these spectra, relative isomerization quantum yields were calculated as a function of excitation energy. While the fluorescence quantum yield drops by a factor of 50-100, the isomerization quantum yields remain essentially constant, implying that the nonradiative process does not directly involve isomerization. On this basis, we postulate that isomerization occurs on the ground-state potential energy surface after internal conversion. In these experiments, the isomerization to naphthalene was not observed, implying a competition between isomerization and cooling on the ground-state potential energy surface.
A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes
Michel, Patrick,Gennet, Dominique,Rassat, Andre
, p. 8575 - 8578 (1999)
Alkynes R-C≡CH were obtained in good yield through a one-pot procedure by a sequence of reactions starting from a Wittig-type condensation of the aldehydes RCHO with the ylide derived from dibromomethyltriphenylphosphonium bromide 5. The same reactions could also be used to prepare the intermediate dibromoalkenes RCH=CBr2, and in certain cases, the bromoalkynes R-C≡CBr.
Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand
Zhao, Jiangui,Zheng, Xueli,Tao, Shaokun,Zhu, Yuxin,Yi, Jiwei,Tang, Songbai,Li, Ruixiang,Chen, Hua,Fu, Haiyan,Yuan, Maolin
, p. 6067 - 6072 (2021/08/16)
The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.
Gold(I)-Catalyzed Oxidative 1,4-Additions of 3-En-1-ynamide with Nitrones via Carbon- versus Nitrogen-Addition Chemoselectivity
Tanpure, Sudhakar Dattatray,Kale, Balaji S.,Liu, Rai-Shung
supporting information, p. 1394 - 1399 (2021/02/20)
This work reports gold-catalyzed 1,4-oxofunctionalizations of 3-en-1-ynamides with nitrones, yielding two distinct E-configured products. We obtained 1,4-oxoarylation products from 3-en-1-ynamides bearing C(4)-electron-donating substituents and 1,4-oxoamination products from those analogues bearing C(4)-aryl substituents. We propose that if vinylgold carbenes are stable, imines undergo a para-arylation on these gold carbenes. If vinylgold carbenes are highly electron-deficient, this N-attack is irreversible to enable 1,4-oxoaminations.
