68826-53-9

Basic information

• Product Name: Benzene, [2-(1-cyclohexen-1-yl)ethenyl]-, (E)-
• CAS NO: 68826-53-9
• Molecular Formula: C14H16
• Molecular Weight: 184.281
• Mol File: 68826-53-9.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: Benzene, [2-(1-cyclohexen-1-yl)ethenyl]-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [2-(1-cyclohexen-1-yl)ethenyl]-, (E)-(68826-53-9)
• EPA Substance Registry System: Benzene, [2-(1-cyclohexen-1-yl)ethenyl]-, (E)-(68826-53-9)

Safety Data

• Hazardous Substances Data: 68826-53-9(Hazardous Substances Data)

Upstream product

• 49639-03-4 (cyclohex-1-enyl)methyl phenyl sulfone 
• 108-24-7 acetic anhydride 
• 100-52-7 benzaldehyde 
• 20109-09-5 1-(phenylethynyl)-1-cyclohexanol 
• 33414-85-6 ((1-methoxycyclohexyl)ethynyl)benzene 
• 59643-63-9 (2-cyclohexylidene ethenyl)-benzene 
• 108-94-1 cyclohexanone 
• 59807-87-3 1-(Benzolsulfonylmethyl)cyclohexanol 
• 110-83-8 cyclohexene 
• 103-80-0 phenylacetyl chloride 
• 31142-52-6 1-(1-cyclohexenyl)-2-phenylethanone 
• 143618-71-7 1-Phenyl-spiro[2.5]octan-4-one 
• 114507-11-8 triphenylphosphonium perchlorate 
• 5330-61-0 1-nitromethyl-cyclohexene 

Downstream Products

• 854220-13-6 2-cyclohex-1-enyl-3-phenyl-oxirane 
• 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 
• 1396021-79-6 (R,E)-N-[N-(S)-(p-toluenesulfonyl)-p-toluenesulfonimidoyl]-3-styrylcyclohex-2-enamine 

Relevant articles and documents

Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System

A redox neutral rearrangement of an allene to a 1,3-diene by means of a unique palladium hydride complex is reported. The palladium hydride complex is generated from a simple Pd 0 source and boric acid [B(OH) 3 ], which is typically identified as a waste by-product of the Suzuki-Miyaura reaction. A mechanism for this transformation using this novel palladium hydride complex is presented; using a direct sample loop and flow injection ESI-HRMS analysis we have detected and identified key π-allylpalladium complexes that support the addition of the palladium hydride complex to the allene.

Synthesis of 1,3-Dienes via a Sequential Suzuki-Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence

We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium-catalyzed, base-free, Suzuki-Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron-donating and -withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid byproduct of the base-free Suzuki-Miyauru coupling, which generates the required palladium-hydrido complex [H-PdII-OB(OH)2] required for the isomerization.

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.