33414-85-6

Upstream product

• 536-74-3 phenylacetylene 
• 108-94-1 cyclohexanone 
• 77-78-1 dimethyl sulfate 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 1004-22-4 (phenylethynyl)sodium 
• 20109-09-5 1-(phenylethynyl)-1-cyclohexanol 
• 933-40-4 cycloxexanone dimethyl ketal 

Downstream Products

• 1200697-79-5 1-(2-cyclohexylidene-1-phenylvinyl)-4-nitrobenzene 
• 1200697-76-2 1-chloro-4-(2-cyclohexylidene-1-phenylvinyl)benzene 
• 1200697-73-9 1-(2-cyclohexylidene-1-phenylvinyl)-4-methylbenzene 
• 59643-63-9 (2-cyclohexylidene ethenyl)-benzene 
• 1200698-11-8 (1-cyclohexylidenepenta-1,4-dien-2-yl)benzene 
• 1200698-14-1 (1-cyclohexylidene-4-methylpenta-1,4-dien-2-yl)benzene 
• 1383536-99-9 4-phenyl-3a,4,7,8,9,9a-hexahydronaphtho[1,2-c]furan-1,3(6H,9bH)-dione 
• 1383537-00-5 2,4-diphenyl-3a,4,6,7,8,9,9a,9b-octahydro-1H-benzo[e]isoindole-1,3(2H)-dione 
• 68826-53-9 (E)-(2-(cyclohex-1-en-1-yl)vinyl)benzene 
• 1422427-17-5 C₂₁H₂₁NO₃ 
• 33493-91-3 trans-1-Phenyl-2-(1'-methoxycyclohexyl)ethylen 

Relevant academic research and scientific papers

Reductive Cleavage of Propargylic Ethers with Alkali Metal: Application to the Synthesis of Allenylboronates

Treatment of propargylic ethers with sodium dispersion in the presence of lithium iodide results in the generation of the corresponding carbanion species via cleavage of the propargylic C-O bond. The anionic species react with trimethoxyborane to yield th

Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes

In this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation-Ferrier reaction to produce functionalized sugars in moderate to excellent yields with high diastereoselectivity.

A General Access to Propargylic Ethers through Br?nsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

A general Br?nsted acid catalyzed methodology for the alkynylation of acetals and ketals with alkynyltrifluoroborate salts has been developed. The reaction proceeds rapidly to afford valuable synthetic building block propargylic ethers in good to excellent yields. Unlike Lewis acid catalyzed transformations of trifluoroborates, this approach does not proceed via unstable organodifluoroborane intermediate. As a result, the developed methodology features excellent functional group tolerance and good atom economy. Br?nsted acid catalyzed alkynylation of acetals and ketals is described. Alkynyltrifluoroborate salts react rapidly to afford propargylic ethers. Organodifluoroborane, which is a common intermediate in Lewis acid catalyzed reactions of trifluoroborates, has not been observed. The reaction exhibits generally high yields and excellent functional group tolerance.

Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

Generation of allenic/propargylic zirconium complexes and subsequent cross-coupling reactions: A facile synthesis of multisubstituted allenes

(Chemical Equation Presented) The β-alkoxide elimination reaction of propargylic ether with Negishi reagent leads to allenes and/or alkynes after hydrolysis. The product distribution is highly dependent on the substitution pattern of starting propargylic