22825-21-4

Basic information

• Product Name: Benzene, 1,1'-(2-cyclopropen-1-ylidene)bis-
• CAS NO: 22825-21-4
• Molecular Formula: C15H12
• Molecular Weight: 192.26
• Mol File: 22825-21-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(2-cyclopropen-1-ylidene)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(2-cyclopropen-1-ylidene)bis-(22825-21-4)
• EPA Substance Registry System: Benzene, 1,1'-(2-cyclopropen-1-ylidene)bis-(22825-21-4)

Safety Data

• Hazardous Substances Data: 22825-21-4(Hazardous Substances Data)

Upstream product

• 119-61-9 benzophenone 
• 13249-58-6 1-bromo-2,2-diphenylethylene 
• 98-86-2 acetophenone 
• 108-86-1 bromobenzene 
• 173595-36-3 3,3-diphenyl-1,1,2-tribromocyclopropane 
• 2592-73-6 1,1-dibromo-2,2-diphenylethylene 
• 530-48-3 1,1-Diphenylethylene 
• 17343-74-7 1,1-dibromo-2,2-diphenylcyclopropane 
• 173595-32-9 C₁₅H₁₁Br 
• 75-77-4 chloro-trimethyl-silane 
• 25229-61-2 p-toluenesulfonyl (3,3-diphenyl-2-propenylidene)hydrazide 
• 32812-52-5 1-bromo-2,2-diphenyl cyclopropane 

Downstream Products

• 83300-55-4 2,5,7,7-tetraphenyl-3,5-(2,2'-diphenylene)-1,3,5-cycloheptatriene 
• 83300-50-9 1,3,3,5-tetraphenyl-6,7-(2,2'-diphenylene)tricyclo<3.2.1.0^2,4>oct-6-en-8-one 
• 1961-97-3 3-phenyl-1H-indene 
• 90909-52-7 (1S,2S,3R)-2-(2,2-Diphenyl-vinyl)-3-methyl-cyclopropanecarboxylic acid methyl ester 
• 90909-53-8 3,3,6,6-Tetraphenyl-trans-tricyclo<3.1.0.0^2,4>hexan 
• 128685-26-7 (3,3-diphenylallenylidene)trimethylphosphanetitanocene 
• 190333-77-8 (3,3-diphenylcyclopropene)[1,2-bis(diphenylphosphino)ethane]platinum 
• 23125-14-6 (E)-1,1,6,6-tetraphenylhexa-1,3,5-triene 
• 172952-34-0 (Z)-1,1,6,6-tetraphenylhexa-1,3,5-triene 
• 120342-72-5 (E)-5,5-diphenyl-2,4-pentadieneoic acid ethyl ester 
• 623-91-6 diethyl Fumarate 
• 141-05-9 Diethyl maleate 

Relevant articles and documents

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.