2450-56-8

Upstream product

• 2450-55-7 diphenyl fumarodinitrile 
• 82193-90-6 2,5-dibromo-3,6-diphenyl-1,4-dithiin-1,1,4,4-tetraoxide 
• 7677-24-9 trimethylsilyl cyanide 
• 501-65-5 diphenyl acetylene 
• 127074-40-2 (phenylethynyl)bis(trimethylsilyl)amine 
• 1246677-86-0 2-bromo-2-iodo-3-phenyl-2H-azirine 

Downstream Products

• 2450-55-7 diphenyl fumarodinitrile 
• 35114-54-6 5-amino-2-imino-3,4-diphenyl-2H-pyrrole 
• 4645-35-6 octaphenyl-meso-tetraazaporphin 
• 173556-81-5 ZnC₈N₈(C₂(C₆H₅)2)((CH₂)8O₅C₆H₂)3 
• 173556-82-6 CuC₈N₈(C₂(C₆H₅)2)((CH₂)8O₅C₆H₂)3 

Relevant academic research and scientific papers

Elusive ethynyl azides: Trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes

Although they decompose rapidly to produce cyanocarbenes, ethynyl azides were generated from (chloroethynyl)arenes and trapped for the first time by 1,3-dipolar cycloaddition at cyclooctyne.

THE SEARCH FOR THE ETHYNYL CATION: NITROSATION OF N,N-BIS(TRIMETHYLSILYL)YNAMINES

The reaction of bis-silylated ynamines with different nitrosyl reagents affords products derived from an electrophilic attack at the β-carbon atom and not the expected alkynyldiazonium salts.

Palladium- and Nickel-Catalyzed Reaction of Trimethylsilyl Cyanide with Acetylenes. Addition of Trimethylsilyl Cyanide to the Carbon-Carbon Triple Bonds

The reaction of trimethylsilyl cyanide (1) with acetylenes in the presence of a transition-metal complex was investigated.The structures of starting acetylenes and catalysts and both amounts of solvent and 1 highly affected product distributions.The PdCl2/pyridine catalyzed reaction of phenylacetylene and para-substituted phenylacetylenes with 1 resulted in the addition of 1 to the carbon-carbon triple bonds to give cyano-substituted vinylsilanes in good to high yields with high regio- and stereoselectivity.Ortho-substituted phenylacetylenes gave addition products less stereoselectively.Stereoselectivity affording Z adducts decreased in the order of para- meta- ortho-substituted phenylacetylenes.The NiCl2/DIBAH-catalyzed reaction of arylacetylenes was less stereoselective regardless of substitution patterns of arylacetylenes used.When the nickel-catalyzed reaction of arylacetylenes was run without solvent using an excess amount of 1, 5-amino-1H-pyrrole-2-carbonitriles were obtained as a single product, instead of the above simple addition products.The reaction of terminal aliphatic acetylenes with 1 also gave addition products with moderate stereoselectivity.Internal acetylenes gave complex mixtures including addition products and/or pyrrole derivatives.Diarylacetylenes afforded 5-amino-1H-pyrrole-2-carbonitriles selectively in the presence of a palladium or nickel catalyst (without solvent and an excess amount of 1).Intramolecular cyclization of a 1,6-diyne was also studied.

REACTIONS OF 2,5-DIPHENYL-1,4-DITHIIN SULFONES WITH SODIUM AZIDE

A number of unanticipitated transformations were observed when various 2,5-diphenyl-1,4-ditiin sulfones were treated with sodium azide.These include a fragmentation to give 1,2-dicyano-1,2-diphenylethene, the formation of 2,5-diphenyl-1,4-thiazine-1,1-dioxide, and the rearrangement of 3-bromo-2,5-diphenyl-1,4-dithiin-1,1-dioxide to its 2-bromo- isomer.Possible mechanism for these unusual reactions are discussed.