79919-09-8

Usage

Chemical structure

1,2,3-triphenylcycloprop-2-ene-1-carbonitrile has a three-membered cyclopropene ring with three phenyl groups attached to it and a cyano group (C≡N) attached to the carbon atom of the cyclopropene ring.

Molecular weight

Approximately 319.39 g/mol

Reactivity

Highly reactive due to the presence of the strained three-membered cyclopropene ring and the electron-withdrawing cyano group.

Stability

Less stable than other aromatic compounds due to the high ring strain in the cyclopropene ring.

Toxicity

Potentially toxic, and its properties and behavior have been studied for potential applications in various areas of chemistry and materials science.

Applications

Used in organic synthesis and chemical research, particularly for the synthesis of other complex organic molecules.

Unique structure

The presence of the strained three-membered cyclopropene ring and the cyano group makes 1,2,3-triphenylcycloprop-2-ene-1-carbonitrile an interesting subject for further investigation and exploration of its potential uses in different fields.

Research interest

The compound's unique structure and reactivity have attracted attention from researchers, who are interested in understanding its potential applications and developing new synthetic methods to access related compounds.

Hazards

Due to its potential toxicity and reactivity, appropriate safety precautions should be taken when handling 1,2,3-triphenylcycloprop-2-ene-1-carbonitrile, including the use of personal protective equipment and working in a well-ventilated area.

Upstream product

• 1483-82-5 phenylethynyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 501-65-5 diphenyl acetylene 
• 61766-63-0 2-diazo-2-phenylacetonitrile 
• 151-50-8 potassium cyanide 
• 51778-20-2 1,2,3-triphenylcyclopropenylium perchlorate 

Downstream Products

• 79919-11-2 1,2,3-triphenyl-3-acetylcyclopropene 
• 79919-10-1 1,2,3-triphenyl-3-formylcyclopropene 
• 137570-31-1 3-benzoyl-1,2,3-triphenylcyclopropene imine 
• 345309-68-4 1-methyl-2,3,4-triphenyl-1,4-dihydrofuran 
• 79919-05-4 (E)-3,4,5-triphenyl-3-pentene-2,5-dione 
• 79919-04-3 (Z)-3,4,5-triphenyl-3-pentene-2,5-dione 
• 79919-15-6 1-(1,2,3-triphenylcyclopropen-1-yl)-ethanol 
• 79919-13-4 3-(hydroxymethyl)-1,2-diphenylindene 
• 79919-14-5 1-methylene-2,3-diphenyl-1H-indene 
• 3263-79-4 2,3,4,5-tetraphenyl-1H-pyrrole 
• 81061-18-9 N-benzyl-N-benzoyl-(1,2,3-triphenylcyclopropen-2-yl)carbinylamine 
• 81061-13-4 N,N-dibenzyl-(1,2,3-triphenyl-cyclopropen-2-yl)carbinylamine 
• 81061-16-7 Benzyl-((2R,3S)-1,2,3-triphenyl-cyclopropylmethyl)-amine 
• 81061-17-8 N-benzyl-(1,2,3-triphenylcyclopropen-2-yl)carbinylamine 

Relevant academic research and scientific papers

Selective Alkynylallylation of the C?C σ Bond of Cyclopropenes

A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C?C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp2)-C(sp3) bond scission with conjunctive cross-couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram-scale products can be easily obtained by such a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations afford a rationale toward the formation of the products and indicate that the selective insertion of the double bond of cyclopropenes into the C-Pd bond of ambidentate Pd complex and the subsequent nonclassical β-C elimination promoted by 1,4-palladium migration are critical for the success of the reaction.

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.

Photochemistry of Cyclopropene Derivatives. Synthesis and Photorearrangement of a 3-Acyl-Substituted Cyclopropene

Two different approaches toward the synthesis of a 3-acyl-substituted 1,2,3-triphenylcyclopropene were investigated.The first involved treating triphenylcyclopropenyl perchlorate with the anion derived from 1,3-dithiane followed by hydrolysis of the resulting dithioacetal.Unfortunately, all attempts to obtain a carbonyl compound from the hydrolysis failed.The only product obtained corresponded to a 1,2-diphenyl-1,2-diacyl-substituted alkene.The second approach utilized for the synthesis involved treating 3-cyano-1,2,3-triphenylcyclopropene with methyllithium.The addition proceeded quite smoothly to give the desired 3-acetyl derivative in high yield.Irradiation of 1,2,3-triphenyl-3-acetylcyclopropene in benzene afforded a mixture of 2,3,4-triphenyl-2-cyclopentenone (60percent), 2-methyl-3,4,5-triphenylfuran (27percent), and 3-acetyl-1,2-diphenylindene (13percent).The formation of the three products obtained can be rationalized in terms of a vinylcarbene intermediate.Several different pathways are available to this species, depending on the stereochemistry about the double bond and on the conformation the oxygen atom assumes in the cis intermediate.The formation of the 2-cyclopentenone derivative provides good support for the mechanism proposed some years ago to rationalize the photochemical rearrangement of 2,5-dimethylfuran.

EFFECTS OF SUBSTITUENTS ON THE TYPE II. PHOTOREACTION OF TETRASUBSTITUTED CYCLOPROPENES

The triplet sensitized behavior of a number of 3-alkyl substituted cyclopropenes containing a heteroatom on the side chain has been studied in mechanistic detail.The triplet state was found to undergo H-atom abstraction by a mechanism analogous to the wel