3018-21-1

Usage

Uses

Used in Organic Synthesis:
1,2-Diphenylcyclobutane is used as a building block in organic synthesis for its unique structural features and reactivity, contributing to the formation of various complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1,2-Diphenylcyclobutane serves as a key intermediate in the synthesis of a range of pharmaceuticals and fine chemicals, leveraging its structural properties to create effective medicinal compounds.
Used in Research and Development:
Due to its intriguing stereochemistry and the strain in its cyclobutane ring, 1,2-Diphenylcyclobutane is used as a research tool in academic and industrial laboratories to explore and develop new chemical reactions and synthetic pathways.
However, it is important to note that the application of 1,2-Diphenylcyclobutane is somewhat restricted due to its relatively high cost and the challenges associated with its synthesis process.

Upstream product

• 7694-30-6 cis-1,2-diphenylcyclobutane 
• 3617-23-0 meso-1,4-dichloro-1,4-diphenylbutane 
• 16844-20-5 1,4-dibromo-1,4-diphenyl-butane 
• 67-64-1 acetone 
• 100-42-5 styrene 
• 66090-52-6 3,6-diphenyl-3,4,5,6-tetrahydropyrazine 
• 23808-18-6 3,6-diphenyl-3,4,5,6-tetrahydropyrazine 

Downstream Products

• 100-42-5 styrene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 74-85-1 ethene 
• 3018-20-0 1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 72887-10-6 1-methoxy-1,4-diphenylbutane 
• 6622-43-1 α,α'-diphenyladipic acid 

Relevant academic research and scientific papers

Effect of Reaction Media on Photosensitized [2+2]-Cycloaddition of Cinnamates

The outcome of photosensitized [2+2]-cycloaddition reactions of various cinnamates has been compared in different reaction media, including homogeneous organic solutions under inert conditions, degassed water, and aerated physical gels. The reactions were performed under LED blue light (λmax=455 nm) irradiation and [Ir{dF(CF3)ppy}2(dtb-bpy)]PF6 (1.0 mol%) as photocatalyst. The processes were optimized taking into consideration solvent, gelator, and substrate. Comparative kinetics analyses, as well as the effect of the reaction media on the diastereoselectivity of the process, were evaluated during this investigation. In a number of cases, carrying out the reaction in a less polar solvent, like toluene or highly polar solvent, like water had a tremendous impact on the diastereoselectivity of the process, pointing towards an effect on the stabilization of the putative diradical intermediate in this medium. Moreover, while for reactions run in homogeneous solution oxygen needs to be excluded, no erosion in yield is observed when the photoadditions were run in aerated gel media.

Method for constructing four-membered ring through visible light catalytic [2+2] reaction

The invention discloses a method for constructing a four-membered ring through visible light catalytic [2+2] reaction. The method comprises the following steps: 1.1) adding an unsaturated double-bondcompound and a photosensitizer into a solvent to obtain a solution A; 1.2) irradiating the solution A by using visible light under the argon atmosphere to obtain a dimerized[2+2]cyclobutane product; or 2.1) adding the unsaturated double-bond compound, a styrene compound and the photosensitizer into a solvent to obtain a solution B; and 2.2) irradiating the solution B by using visible light under the argon environment to obtain a crossed [2+2]cyclobutane product. The visible light sensitizer is utilized for the first time and non-rigid double-bond intermolecular[2+2]cyclization reaction is realized; the use amount of the light sensitizer is small, the reaction can be realized under the argon environment by utilizing the visible light or sunlight, and the reaction condition is mild; and thewhole process is simple and efficient, and potential application in organic reaction and industrial production is embodied.

Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes

An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong π-π-stacking of arene moieties, whereas diastereoselectivity relies on the electronic effects or ortho-substitution of the arene substrate. The utility of this transformation is demonstrated by the formal synthesis of the lignane natural product (±)-Tanegool.

Visible light-induced highly selective transformation of olefin to ketone by 2,4,6-triphenylpyrylium cation encapsulated within zeolite Y

2,4,6-Triphenylpyrylium cation encapsulated within zeolite Y promotes highly selective transformation of olefins to ketones with molecular oxygen, under visible light (λ > 400 nm) irradiation at room temperature. The Royal Society of Chemistry 2006.

Two-photon generation of the 1,4-diphenyl-1,4-butanediyl biradical: Direct detection and product studies

The 1,4-diphenyl-1,4-butanediyl biradical (3) is generated from 1,4- dichloro-1,4-diphenylbutane (1) or 2,5-diphenylcyclopentanone (8) under several irradiation conditions. The products resulting from this intermediate are styrene (4), 1,2-diphenylcyclobutane (5), and 1-phenyl-1,2,3,4- tetrahydronaphthalene (6). The formation of tetrahydronaphthalenes appears to be a fingerprint for the intermediacy of 1,4-biradicals having a phenyl group attached to one of the radical centers as corroborated in the high-intensity irradiation of 2-phenylcyclopentanone (12). The yield of 6 depends on the substrate and irradiation conditions; this is rationalized as due to a conformational memory effect of the nascent biradical.

Photochemical Generation of 1,4-Diphenylbutane-1,4-diyl

Photochemical deazetation of 3,6-diphenyl-3,4,5,6-tetrahydropyrazine (1) was re-examined; evidence was obtained for trapping of a diradical intermediate (2) by oxygen when (1) was photolysed in the absence of solvent.

Thermal Ring-Splitting Reactions of Diarylcyclobutanes: Significance of Steric Effects on Orbital Interactions in Transition States and Biradical Intermediates

Regiochemistry and rectivities in the thermal ring-splitting reactions of diarylcyclobutanes (1-5) have been studied and shown to depend on the stable conformations and rotational mobilities of the aryl substituents.The reactions of 1 and 2 result in a regiospecific symmetric cleavage to give indene or styrene along with significant isomerization of 2 to 3.In the cases of 3-5 both the symmetric and unsymmetric cleavages competitively occur with decreasing symmetric-to-unsymmetric ratios with an increase in methyl substitution.The olefin products from 4 are mixtures of cis- and trans-2-butene, cis- and trans-β-methylstyrene, and trans-stilbene.Thermochemical analyses combined with product analyses indicate that the symetric cleavage of 1 and the unsymmetric cleavage of 3 proceed with a concerted mechanism, whereas 1,4-biradicals are involved in the other reactions.Structure-reactivity relationships of the present reactions are discussed in terms of mixing of the ?* character in a bonding MO by specific ?-?* interactions, depending on the conformational situations of the aryl groups and in terms of the steric effects which destabilize 1,4-biradicals as well as transition states of the biradical fragmentation to the olefins.

Photochemical Reaction of Aromatic Compounds. XLVI. Stereochemical Reactions Courses in the Photolytic Ring-Cleavage Reactions of Diarylcyclobutanes:Implications of Conformation-Controlled Orbital Interactions in the Excited-State Chemistry

The photolyses of cis-transoid-cis-cyclobutadiindene (1), cis-2-phenylcyclobutindene (2), cis-1,2-diphenylcyclobutane (3), the trans isomer (4), and its dimethyl (5) and tetramethyl (6) derivatives have been investigated to explore stereoelectronic factors controlling the excited-state reaction courses for the ring cleavages.The symmetric ring cleavage occurs regiospecifically in the cases of 1-3 and with 98percent specificity in the case of 4.The photolysis of 5 results in both the symmetric and the asymmetric cleavages in a ca. 1:3 ratio accompanied by substantial losses of stereointegrity in the olefin formation, and the regiospecific asymmetric cleavage occurs in the case of sterically more congested 6.The ring-cleavage efficiencies systematically decrease in the order 1>2>3>4>5>6 and reveal negative temperature dependences, particularly in the cases of 1, 5, and 6.The features of the reactions are in parallel with stable conformations and conformational mobilities of the aryl groups associated with different ?-? orbital interactions, while the spectroscopic properties of the cyclobutanes are essentially identical with those of benzene chromophores with little electronic perturbation.The photolitic ring-cleavage reactions are discussed in terms of crossing from the localized 1?,?* state to a ?* hypersurface, in wich conformation-controlled orbital interactions play important roles.The final products are formed via a pericyclic minimum which might be biradicaloid in nature.

Photochemical Reactions of Aromatic Compounds. XLII. Photosensitized Reactions of Some Selected Diarylcyclobutanes by Aromatic Nitriles and Chloranil. Implications of Charge-Transfer Contributions on Exciplex Reactivities

Photosensitized reactions of cis- and trans-1,2-diphenylcyclobutane and cis-transoid-cis-cyclobutadiindene by 1-cyanonaphthalene, 9,10-dicyanoanthracene, 1,4-dicyanonaphthalene, and chloranil, which mainly give the ring-splitting product (styrene or indene), have been investigated to explore steric and electronic requirements of the reactions associated with charge-transfer and excitation-resonance contributions of exciplex intermediates.The reaction efficies increase with an increase in the electron-accepting power of the sensitizers irrespective of the spin states.The formation of 1-phenyltetralin in the photosensitized reactions of the diphenylcyclobutanes occurs from the polar singlet exciplex with the dicyanoarenes but not at all from the less polar exciplex with 1-cyanonaphthalene nor from the triplet chloranil exciplex of high charge-transfer nature.Exciplex reactivities are discussed in terms of roles of charge-transfer contributions in exciplex decay channels as well as in terms of configurational and conformational effects on orbital interactions in the cyclobutanes.