3282-18-6

Basic information

• Product Name: 1,1-Diphenylcyclopropane
• Synonyms: 1,1-Diphenylcyclopropane
• CAS NO: 3282-18-6
• Molecular Formula: C₁₅H₁₄
• Molecular Weight: 194.27166
• Mol File: 3282-18-6.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 140 °C
• Appearance: /
• Density: 1.0330 g/cm3
• CAS DataBase Reference: 1,1-Diphenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Diphenylcyclopropane(3282-18-6)
• EPA Substance Registry System: 1,1-Diphenylcyclopropane(3282-18-6)

Safety Data

• Hazardous Substances Data: 3282-18-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2467, 1989 DOI: 10.1021/jo00271a048

Upstream product

• 186581-53-3 diazomethane 
• 530-48-3 1,1-Diphenylethylene 
• 60-29-7 diethyl ether 
• 623-73-4 diazoacetic acid ethyl ester 
• 20763-38-6 (3,3-diphenyl-propyl)-trimethyl-ammonium; iodide 
• 101-81-5 Diphenylmethane 
• 109-72-8 n-butyllithium 
• 100762-31-0 (S)-(+)-1-chloro-2,2-diphenylcyclopropane 
• 882-59-7 1,1-diphenyloxirane 
• 76373-10-9 (trimethylstannyl)methyl-lithium 
• 132776-00-2 (+)-(S)-1-fluoro-1-iodo-2,2-diphenylcyclopropane 
• 74-85-1 ethene 
• 19255-91-5 (2-chlorocyclopropane-1,1-diyl)dibenzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Downstream Products

• 127931-45-7 C₂₅H₁₈Cl₂O₂ 
• 120062-19-3 1-Chloro-1-diisopropylamino-2,2-diphenyl-phosphetanium 
• 778-66-5 1,1-diphenyl-1-propene 
• 26461-03-0 1-phenylindane 
• 1530-03-6 1,1-diphenylpropane 
• 64884-65-7 3-Bromo-1,1-diphenyl-prop-1-yl-hydroperoxide 
• 42558-10-1 1,1-bis-(4-nitrophenyl)cyclopropane 
• 38899-54-6 2-methyl-5,5-diphenyl-2-pentanol 

Relevant articles and documents

Oxidative addition of a strained C-C bond onto electron-rich rhodium(I) at room temperature

The C-C bond of cyclobutanones undergoes oxidative addition to a T-shape rhodium(I) complex possessing a PBP pincer ligand at room temperature. The remarkable propensity of the rhodium complex for oxidative addition is attributed to the highly electron-donating nature of the boron ligand as well as the unsaturation on the rhodium center.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes

A highly stereocontrolled syn-addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper-catalyzed C?Si bond formation closes the gap of the direct synthesis of α-chiral cyclopropylsilanes.

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.