1138-48-3

Usage

Uses

Used in Organic Synthesis:
(cis)-1,1'-(1,2-cyclopropanediyl)bisbenzene is utilized as a building block for the construction of larger and more complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of a variety of compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (cis)-1,1'-(1,2-cyclopropanediyl)bisbenzene is employed as a starting material for the synthesis of various pharmaceuticals. Its specific geometry allows for the creation of molecules with targeted biological activities, contributing to the development of new drugs.
Used in Agrochemical Synthesis:
Similarly, in agrochemical applications, (cis)-1,1'-(1,2-cyclopropanediyl)bisbenzene is used as a starting material for synthesizing compounds with pesticidal or herbicidal properties. Its structural features facilitate the design of effective agrochemicals.
Used in Laboratory Research:
(cis)-1,1'-(1,2-cyclopropanediyl)bisbenzene also plays a significant role in laboratory research, where it is used to explore the properties and reactions of organic compounds. Its presence in research settings aids in advancing the understanding of organic chemistry and the development of novel synthetic pathways.

Upstream product

• 100-42-5 styrene 
• 100-52-7 benzaldehyde 
• 53422-72-3 3,5-Diphenyl-Δ²-pyrazolin 
• 59891-90-6 cis-3,5-Diphenyl-1-pyrazoline 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 159956-91-9 ((1R,3S)-3-Chloro-1,3-diphenyl-propyl)-triphenyl-silane 
• 145134-45-8 Benzenesulfonic acid (1S,3R)-1,3-diphenyl-3-tributylstannanyl-propyl ester 
• 145134-42-5 Benzenesulfonic acid (1R,3R)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 145134-42-5 Benzenesulfonic acid (1R,3S)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 75765-74-1 (+)-trans-3,5-diphenyl-1-pyrazoline 
• 34462-03-8 trans-N-nitroso-2,4-diphenylazetidine 
• 34462-03-8 cis-N-nitroso-2,4-diphenylazetidine 
• 10514-16-6 trans-3,5-Diphenyl-1-pyrazoline 
• 1138-47-2 trans-1,2-diphenylcyclopropane 

Downstream Products

• 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 
• 53215-16-0 3,5-diphenyl-4-nitro-1,2-oxazole 
• 2039-49-8 3,5-diphehylisoxazole 
• 4894-23-9 3,5-diphenyl-4,5-dihydro-isoxazole 
• 3412-44-0 1,3-diphenylpropene 
• 1081-75-0 1,3-diphenylpropane 
• 1138-47-2 trans-1,2-diphenylcyclopropane 
• 51040-96-1 rac-cis-1,2-bis(4-fluorophenyl)cyclopropane 
• 17990-73-7 cis-3,5-diphenyl-1,2-oxathiolane (2,3-trans)-2-oxide 
• 17990-73-7 (+/-)-(2S,3S,5R)-3,5-diphenyl-1,2-oxathiolane 2-oxide 
• 17990-73-7 trans-3,5-diphenyl-1,2-oxathiolane (2,3-cis)-2-oxide 

Relevant academic research and scientific papers

All at once arrangement of both oxygen atoms of dioxygen into aliphatic C(sp3)-C(sp3) bonds for hydroxyketone difunctionalization

Both β- and γ- hydroxyketone structures are important units in biologically active molecules, synthetic drugs and fine chemicals. Although there are some routes available for their manufacture from pre-functionalized groups on one or two matrix molecule(s), the approaches to simply and simultaneously deposit two oxygen atoms from dioxygen into two specific C(sp3) positions of pure saturated hydrocarbons have rarely succeeded because they are involved in the targeted activation of three inert C-H σ bonds all at once. Here, we show that a TiO2-CH3CN photocatalytic suspension system enables the insertion of dioxygen into one C(sp3)-C(sp3) bond of strained cycloparaffin derivatives, by which difunctionalized hydroxyketone products are obtained in a one-pot reaction. With the cleavage event to release strain as the directional driving force, as-designed photocatalytic reaction systems show 21 examples of β-hydroxyketone products with 31%–76% isolated yields for three-membered ring derivatives and 5 examples of γ-hydroxyketone products with 30%–63% isolated yields for four-membered ring substrates. 18O isotopic labeling experiments using 18O2, Ti18O2 and intentionally added H218O, respectively, indicated that both oxygen atoms of hydroxyketone products were exclusively from dioxygen, suggesting a previously unknown H+/TiO2-e? catalyzed arrangement pathway of the hydroperoxide intermediate to convert dioxygen into hydroxyketone units. [Figure not available: see fulltext.]

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.

Modular enantioselective synthesis of cis-cyclopropanes through self-sensitized stereoselective photodecarboxylation with benzothiazolines

Chiral cis-cyclopropanes are strained rigid analogues of alkyl chains, whose study and application are limited by their difficult synthesis. A modular approach from olefin materials is enabled by the discovery of the electron donor-acceptor (EDA) interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, and the benzothiazoline reagent plays a triple role as a photoreductant, a stereoselective hydrogen-atom donor, and a Br?nsted acid. Beyond the enantioselective synthesis of cis-cyclopropanes, these results introduce benzothiazolines as accessible and easily tunable self-sensitized photoreductants.

Gold Sulfonium Benzylide Complexes Undergo Efficient Benzylidene Transfer to Alkenes

The gold sulfonium benzylide complexes [(P1)AuCHPh(SR1R2)]+ {B[3,5-CF3C6H3]4}? [P1=P(tBu)2o-biphenyl; R1, R2=-(CH2)4- (1 a); R1=Et, R2=Ph (1 b); R1=R2=Ph (1 c)] were synthesized by reaction of the gold α-chloro benzyl complex (P1)AuCHClPh with sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate and excess sulfide. Complexes 1 undergo efficient benzylidene transfer to alkenes and DMSO under mild conditions without external activation. Kinetic analysis of the reaction of 1 c with styrene was consistent with the intermediacy of the cationic gold benzylidene complex [(P1)AuCHPh]+ (I).

Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds

The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a safe and user-friendly one-pot iron-catalyzed cyclopropanation reaction is described. Easily synthesized N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds under mild reaction conditions and their direct participation in the cyclopropanation reaction.

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

Nanoscaled copper metal-organic framework (MOF) based on carboxylate ligands as an efficient heterogeneous catalyst for aerobic epoxidation of olefins and oxidation of benzylic and allylic alcohols

Aerobic epoxidation of olefins at a mild reaction temperature has been carried out by using nanomorphology of [Cu3(BTC)2 ] (BTC = 1,3,5-benzenetricarboxylate) as a high-performance catalyst through a simple synthetic strategy. An aromatic carboxylate ligand was employed to furnish a heterogeneous copper catalyst and also serves as the ligand for enhanced catalytic activities in the catalytic reaction. The utilization of a copper metal-organic framework catalyst was further extended to the aerobic oxidation of aromatic alcohols. The shape and size selectivity of the catalyst in olefin epoxidation and alcohol oxidation was investigated. Furthermore, the as-synthesized copper catalyst can be easily recovered and reused several times without leaching of active species or significant loss of activity.

Improved zinc-catalyzed simmons-smith reaction: Access to various 1,2,3-trisubstituted cyclopropanes

The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

Encapsulated cobalt-porphyrin as a catalyst for size-selective radical-type cyclopropanation reactions

A cobalt-porphyrin catalyst encapsulated in a cubic M8L 6 cage allows cyclopropanation reactions in aqueous media. The caged-catalyst shows enhanced activities in acetone/water as compared to pure acetone. Interestingly, the M8L6 encapsulated catalyst reveals size-selectivity. Smaller substrates more easily penetrate through the pores of the "molecular ship-in-a-bottle catalysts" and are hence converted faster than bigger substrates. In addition, N-tosylhydrazone sodium salts are easy to handle reagents for cyclopropanation reactions under these conditions.