1138-47-2

Usage

Uses

Used in Organic Chemistry:
(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene serves as a key intermediate in the synthesis of various organic compounds due to its reactive cyclopropane group and the stability provided by the benzene rings. Its unique structure facilitates multiple types of chemical reactions, making it a versatile component in organic synthesis.
Used in Material Science:
In the field of material science, (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene is utilized as a precursor for developing new materials with specific properties. The cyclopropane group's reactivity allows for the creation of polymers and other materials with tailored characteristics, such as enhanced stability or specific interactions with other molecules.
Used in Pharmaceutical Development:
The unique structure and properties of (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene also make it a promising candidate in pharmaceutical research. Its potential applications include the development of new drugs and drug delivery systems, where its reactivity and molecular interactions can be harnessed to improve therapeutic efficacy and targeting.
Used in the Synthesis of Advanced Polymers:
(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene is employed as a monomer in the synthesis of advanced polymers with specific properties. The cyclopropane group can be manipulated to create polymers with unique mechanical, thermal, or chemical characteristics, suitable for various high-performance applications.

Upstream product

• 100-42-5 styrene 
• 16619-60-6 3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 10514-16-6 trans-3,5-Diphenyl-1-pyrazoline 
• 84064-86-8 C₁₅H₁₃Li 
• 34462-03-8 cis-N-nitroso-2,4-diphenylazetidine 
• 34462-03-8 trans-N-nitroso-2,4-diphenylazetidine 
• 145134-42-5 Benzenesulfonic acid (1R,3S)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 145134-42-5 Benzenesulfonic acid (1R,3R)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 23020-16-8 (1S,2S)-1,2-diphenylcyclopropane 
• 20282-89-7 ((tert-butylsulfonyl)methyl)benzene 
• 591-50-4 iodobenzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 17763-67-6 Phenyl triflate 
• 3412-44-0 (1E)-1,3-diphenylpropene 

Downstream Products

• 26278-69-3 1,3-diphenyl-1,3-dimethoxy propane 
• 109423-45-2 C₃₁H₂₂N₂ 
• 109423-45-2 C₃₁H₂₂N₂ 
• 109423-45-2 6,7:8,9-dibenzo-1,5-dicyano-cis-2,4-diphenylbicyclo<3.2.2>nona-6,8-diene 
• 109423-45-2 6,7:8,9-dibenzo-1,5-dicyano-trans-2,4-diphenylbicyclo<3.2.2>nona-6,8-diene 
• 90095-72-0 (+/-)-trans-1,2-di(p-iodophenyl)cyclopropane 
• 90095-71-9 (+/-)-1,3-bis(trifluoroacetoxy)-1,3-diphenylpropane 
• 4894-23-9 3,5-diphenyl-4,5-dihydro-isoxazole 
• 1138-48-3 cis-1,2-diphenylcyclopropane 
• 3471-09-8 (1R,2R)-1,2-diphenylcyclopropane 
• 3412-44-0 1,3-diphenylpropene 
• 1081-75-0 1,3-diphenylpropane 
• 23020-16-8 (1S,2S)-1,2-diphenylcyclopropane 
• 17714-40-8 1,3-Dibromo-1,3-diphenylpropane 

Relevant academic research and scientific papers

The nickel and palladium catalyzed stereoselective cross coupling of cyclopropyl nucleophiles with aryl halides

The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with good yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)4. Other Ni- and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.

Di-π-methane photorearrangement of trans-1,3-diphenylpropene upon excitation to higher singlet states in polar solvents

A dramatic enhancement of the di-π-methane rearrangement is observed upon excitation of trans-1,3-diphenylpropene (1) to its higher singlet states in acetonitrile, which leads to trans-1,2-diphenylcyclopropane (3) as a major photoproduct.

Kinetische und mechanistische Untersuchungen von Uebergangsmetall-Komplex-Reactionen.XVII. Untersuchungenen zur Substituentenabhaengigkeit der cis/trans-Cyclopropan-Produktherhaeltnisse bei der Uebertragung von Benzylidenliganden auf Styrole

The benzylidene complexes (CO)5M=C(C6H4R-p)H react with styrenes, H2C=C(C6H4R-p)H (R = F, Cl, Br, H, Me, OMe), α-methylstyrene, vinylcyclohexane and 2-methyl-2-butene, respectively, by transfer of the benzylidene ligand to the C=C bond and formation of cis- and trans-cyclopropanes.From the temperature dependence of the cis/trans isomer ratios the differences in the activation enthalpies ΔΔH* = Δ(Hcis)* - Δ(Htrans)* and activation entropies ΔΔS* = Δ(Scis)* - Δ(Strans)* weredetermined.With all reactions the formation of the cis-isomer is favoured by the lower activation enthalpy.The formation of the trans-isomers, however, is generally favoured by the lower activation entropy.Exceptions are the reactions of 1a with styrene and of 1c with 2-methyl-2-butene.These two opposing influences determine the cis/trans isomer ratio observed.The results are discussed on the basis of stabilizing electronic and destabilizing steric interactions.

Palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with aryl triflates

In the presence of appropriate base and NaBr, the Suzuki- type reaction of aryl triflates and trans-cyclopropylboronic acids proceed readily to give pure trans-cyclopropylarenes in good to high yields. For the reaction of general aryl triflates, the base KF·2H2O is efficient, but in the case of aryl triflates bearing electron donating groups, KF·2H2O as a base makes the unexpected phenylaryl exchange between the phenyl of Pd(PPh3)4 and the aryl of triflate to occur. The use of K3PO4·3H2O instead of KF·2H2O can inhibit the unexpected phenyl-aryl exchange, but the yield of the product is somewhat decreased. The coupling reaction of aryl triflates with the optically active cyclopropylboronic acids, which were easily obtained in good yield and with good to excellent ee (up to 94%) by the asymmetric cyclopropanation of alkenylboronates with optically pure TMTA auxiliary, was also investigated. During the coupling reaction, the absolute configuration of the cyclopropyl group was retained. Thus, a novel method to prepare aryl- substituted cyclopropanes, including highly optically active cyclopropanes, from phenols or arylamines was provided.

On the synthesis of aryl cyclopropanes from γ-benzenesulfonylalkyl tin derivatives and n-butyllithium

γ-Benzenesulfonyloxyalkyl tin derivatives readily available from γ-hydroxyalkyl selenides, n-butyllithium and trialkyl tin chlorides react with n-butyllithium and stereospecifically lead to aryl cyclopropanes. The transformation is quite general and allows the synthesis of α,β-di- and trisubstituted ones.

Preparation and applications of a novel bis(tributylstannyl)cyclopropane: A synthetic equivalent of a cyclopropane-1,2-dianion

The preparation of the novel trans-1,2-bis-stannylcyclopropane 4 is described. Its applications in Kosugi-Migita-Stille cross-coupling and in tin-lithium exchange reactions are presented and discussed.

Cyclopropanation of styrenes and stilbenes using lithiomethyl trimethylammonium triflate as methylene donor

Lithiomethyl trimethylammonium triflate, prepared from tetramethylammonium triflate, cyclopropanates several styrenes and stilbenes with electron-donating and selected electron-withdrawing substituents efficiently. Kinetic data support a stepwise nucleophilic addition-ring closure mechanism for this methylenation. This journal is the Partner Organisations 2014.

The Photochemical Debromination of Bromocyclopropane in the Presence of Amine

The irradiation of bromocyclopropanes (1) in the presence of tertiary amine rresulted in the formation of the debrominated cyclopropanes as a mixture of geometrical isomers, whose ratios were essentially similar regardless of the stereochemistry of the bromide.The reactions were not, however, observed in the absence of amine.The results are interpreted as indicating that the reactions proceed through an initial single-electron transfer to the excited 1, followed by debromination and hydrogen-abstraction.

Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal

Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound

The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.