20264-56-6

Upstream product

• 94994-67-9 1,6-dichloro-1,6-diphenyl-hexa-2,4-diyne 
• 5701-81-5 buta-1,3-diynylbenzene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 591-50-4 iodobenzene 
• 879560-03-9 (3-dibromomethylene-penta-1,4-diynyl)-benzene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 470671-32-0 tert-butyl-dimethyl-(4-phenyl-buta-1,3-diynyl)-silane 
• 15814-30-9 1,5-diphenyl-penta-1,4-diyn-3-one 
• 154266-43-0 [3-(dibromomethylene)penta-1,4-diyne-1,5-diyl]dibenzene 
• 536-74-3 phenylacetylene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 17338-03-3 1,6-diphenylhexa-2,4-diyne-1,6-diol 
• 13603-85-5 (3-phenylprop-2-yne-1-sulfonyl)benzene 

Downstream Products

• 1087-49-6 1,6-diphenylhexane 
• 106507-59-9 1-(1'-phenylethynyl-2',2',3',3'-tetramethylcyclopropyl)-2-(1-phenyl-2,2,3,3-tetramethylcyclopropyl)acetylene 
• 142144-53-4 (Z)-1,6-diphenyl-1-phenylthio-hex-1-en-3,5-diin 
• 142144-54-5 (Z,Z)-1,6-Diphenyl-1,6-bis(phenylthio)hexa-1,5-dien-3-in 
• 113860-49-4 1-(1-phenyl-2,2,3,3-tetramethylcyclopropyl)-2-(1-(phenylethynyl)-2-cyanocyclopropyl)acetylene 

Relevant academic research and scientific papers

A new type of carborane-based electron-accepting material

In this study, a new type of carborane-based electron acceptor was prepared by the direct attachment of an ethynyl group to the carboranyl carbon atom. Analyses of photophysical and electrochemical and DFT calculations suggested that the direct attachment of the ethynl group significantly affects the electrochemical properties of these o-carborane systems. This journal is

Unraveling the Mechanism of 1,3-Diyne Cross-Metathesis Catalyzed by Silanolate-Supported Tungsten Alkylidyne Complexes

The benzylidyne complex [PhC≡W{OSi(OtBu)3}3] (1) catalyzed the cross-metathesis between 1,4-bis(trimethylsilyl)-1,3-butadiyne (2) and symmetrical 1,3-diynes (3) efficiently, which gave access to TMS-capped 1,3-diynes RC≡C?C≡CSiMesub

Synthesis of unsymmetrical 1,3-diynes via alkyne cross-metathesis

The tungsten benzylidyne complex [PhC≡W{OSi(OtBu)3} 3] (1) efficiently catalyses the metathetic conversion between symmetrical and unsymmetrical 1,3-diynes, which provides the opportunity to prepare the latter species directly from terminal alkynes by a combination of copper-catalysed homocoupling and catalytic alkyne cross-metathesis (ACM).

Synthesis and 13C NMR spectroscopy of 13C-labeled α,ω-diphenylpolyynes

The synthesis of three 13C-labeled α,ω- diphenylpolyynes is described. The known positions of the labeled carbon atoms allow assignment of the resonances in the 13C NMR spectra and identification of trends in the chemical shifts. Geo

Investigation of an efficient palladium-catalyzed C(sp)-C(sp) cross-coupling reaction using phosphine-olefin ligand: Application and mechanistic aspects

A π-acceptor phosphine-electron-deficient olefin ligand was found effective in promoting Pd-catalyzed C(sp)-C(sp) cross-coupling reactions. The new protocol realized the cross-coupling of a broad scope of terminal alkynes and haloalkynes in good to excellent yields with high selectivities. Electron-rich alkynes, which are normally difficult substrates in Glaser couplings, could be employed as either nucleophiles or electrophiles. Alkynes bearing similar substituents, such as n-C5H11CCBr and n-C4H9CCH, which usually suffer from homocoupling side reactions under Cadiot-Chodkiewicz conditions, were successfully cross-coupled in the system. Preliminary kinetic studies revealed that the reaction rate was zero-order in the concentrations of both haloalkynes and terminal alkynes and first order in the loading of Pd(dba)2 and exhibited no obvious dependence on the loading of the copper salt. Control experiments with other phosphines such as PPh3 and DPPF as the ligand were carried out. All the kinetic evidence indicated that the phosphine-olefin ligand facilitated the reductive elimination in the catalytic cycle.

One-pot formation and derivatization of di- and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement

(Chemical Equation Presented) A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement is used to gene

A one-pot synthesis and functionalization of polyynes

A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li-acetylide is then trapped in situ with an electrophile to pro

Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones. Copyright

Expanded Radialenes with Bicyclo[4.3.1]decatriene Units: New Precursors to Cyclo[n]carbons

A new method for the formation of conjugated polyynes has been developed based on both the rearrangement of vinylidenes to alkynes and the [2+1] cheletropic fragmentation of dialkynylmethylenebicyclo-[4.3.1]deca-1,3,5-triene derivatives. A model study of the photolysis of simple dialkynylmethylenebicyclo[4.3.1]deca-1,3,5-trienes resulted in cheletropic fragmentation followed by 1,2-migration to give the corresponding linear polyynes, although undesired isomerization to methylenebicyclo[5.3.0]triene derivatives took place concurrently. Expanded [3]-, [4]-, [5]-, and [6] radialene derivatives with exocyclic bicyclo[4.3.1]decatriene units were prepared by oxidative coupling of the monomeric units as precursors to the corresponding cyclo[n]carbons, monocyclic forms of carbon clusters. The spectroscopic properties of the expanded radialenes were investigated in connection with cross conjugation of the core π system and with its perturbation by the extraannular bicyclic π system. In negative-mode laser-desorption time-of-flight (LD-TOF) mass spectra, the expanded radialenes exhibited peaks due to the corresponding cyclo[n]carbon anions (n = 18, 24, 30, and 36) formed by the stepwise loss of the aromatic indane fragments.

Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes

A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.