1674-16-4

Basic information

• Product Name: Benzene, 1,1',1'',1'''-(1,2,3,4,5-hexapentaene-1,6-diylidene)tetrakis-
• CAS NO: 1674-16-4
• Molecular Formula: C30H20
• Molecular Weight: 380.489
• Mol File: 1674-16-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1',1'',1'''-(1,2,3,4,5-hexapentaene-1,6-diylidene)tetrakis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1',1'',1'''-(1,2,3,4,5-hexapentaene-1,6-diylidene)tetrakis-(1674-16-4)
• EPA Substance Registry System: Benzene, 1,1',1'',1'''-(1,2,3,4,5-hexapentaene-1,6-diylidene)tetrakis-(1674-16-4)

Safety Data

• Hazardous Substances Data: 1674-16-4(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 3923-52-2 1,1-diphenyl-2-propyn-1-ol 
• 60-29-7 diethyl ether 
• 108-24-7 acetic anhydride 
• 20583-04-4 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol 
• 110-86-1 pyridine 
• 119-61-9 benzophenone 
• 3848-49-5 1,1-diphenyl-2-propyn-1-yl acetate 

Downstream Products

• 57690-94-5 1,1,6,6-Tetraphenyl-hexatetraen-(1,2,4,5) 
• 97076-00-1 ((1E,5E)-1,6,6-triphenylhexa-1,5-dien-3-ynyl)benzene 
• 120446-31-3 1,2-bis(3,3-diphenylallenylidene)-3,4-bis(diphenylmethylene)cyclobutane 
• 119-61-9 benzophenone 
• 20583-04-4 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol 
• 131207-57-3 (C₆H₅)2CCC(Pt(P(C₆H₅)3)2)CCC(C₆H₅)2 
• 131207-55-1 chloro(tetraphenylhexapentaene)bis(triphenylphosphine)rhodium 
• 141229-80-3 hexcarbonyl(tetraphenylhexapentaene)diiron 
• 96376-96-4 1,1,6,6-Tetraphenyl-hexatetraen-(1,2,3,5) 
• 172952-34-0 (Z)-1,1,6,6-tetraphenylhexa-1,3,5-triene 
• 23125-14-6 (E)-1,1,6,6-tetraphenylhexa-1,3,5-triene 
• 2819-41-2 1,1,6,6-tetraphenylhexane 

Relevant articles and documents

Thermal cyclotrimerization of tetraphenyl[5]cumulene (tetraphenylhexapentaene) to a tricyclodecadiene derivative

Tetraphenyl[5]cumulene (tetraphenylhexapentaene) underwent cyclotrimerization in refluxing toluene for 10-15 min to give a tricyclodecadiene derivative in 68% yield. The Royal Society of Chemistry.

Nickel-catalyzed dimerization of [5]cumulenes (Hexapentaenes)

Tetraaryl[5]cumulenes react with low-valent nickel complexes at the second double bond to produce novel [4]radialene derivatives that are head-to-head dimers of [5]cumulenes. The head-to-head dimers are also synthesized by a stepwise route. On the other hand, the nickel-catalyzed dimerization of [5]cumulenes with bulky substituents produces other types of extended [4]radialenes and [5]radialenones depending on the bulkiness of the terminal alkyl substituents. Thus, tetrakis-t-butyl[5]cumulene and 1,4-bis(2,2,6,6- tetramethylcyclohexylidene)[3]cumulene react at the central double bond to give the corresponding [4]radialene and [5]radialenone, whereas 1,4-bis(2,2,5,5- tetramethylcyclopentylidene)[3]cumulene and its benzo-annelated derivative react at the second double bond in a head-to-tail manner to afford the corresponding extended [4]radialenes. Tetrakis-t-butyl[5]radialenone was converted into [5]radialene by using a methylation-dehydration procedure. The extended [4]- and [5]radialenes and [5]radialenones have been fully characterized by spectroscopic analyses, X-ray crystallography, and/or independent chemical synthesis. The properties of these novel exocyclic π-electron systems have been investigated in detail. The aryl-substituted [4]radialenes exhibit facile bond rotation with low energy barriers. The [5]radialene and [5]radialenone form the corresponding cations easily by the addition of an acidic proton. The selectivity of the nickel-catalyzed dimerization of [5]cumulenes is discussed on the basis of theoretical calculations.