28480-27-5

Upstream product

• 67-66-3 chloroform 
• 61440-86-6 bis(4-tert-butylphenyl)acetylene 
• 64321-35-3 4-(1,1-Dimethylethyl)phenylmethyl ketone 
• 32857-63-9 4-t-butylphenylacetic acid 
• 6262-42-6 1,2,3,3-tetrachlorocyclopropene 
• 253185-03-4 tert-butylbenzene 

Downstream Products

• 86193-98-8 2,3-Bis-(4-tert-butyl-phenyl)-1-hydroxy-indolizine-7-carboxylic acid methyl ester 
• 28488-88-2 10-[2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-2,3-dimethyl-10H-anthracen-9-one 
• 28488-86-0 12-[2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-12H-benzo[a]anthracen-7-one 
• 28488-87-1 12-[2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-12H-naphthacen-5-one 
• 28488-80-4 2-[2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-1-phenyl-butane-1,3-dione 
• 28480-26-4 [2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-(4-nitro-phenyl)-amine 
• 28488-81-5 2-[2,3-Bis-(4-tert-butyl-phenyl)-cycloprop-2-enylidene]-3-oxo-3,N-diphenyl-propionamide 

Relevant academic research and scientific papers

Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides

Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.

Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles

Represented is a CuX2- or I2-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C–X (X = Cl, Br, or I) bonds and a C–O bond as well as the cleavage of two C–O bonds and a C–C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.

Organocatalytic Regiodivergent C?C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks

Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain-release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen-bonding network activation and a regiodivergent strain-assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring-loaded” intermediate with switchable C?C bond cleavages achieved by controllable ring-strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.

Development of a catalytic platform for nucleophilic substitution: Cyclopropenone-catalyzed chlorodehydration of alcohols

Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.