3306-02-3

Usage

Uses

Used in Chemical Synthesis:
1,2-Diphenylcyclobutene is used as an intermediate in the synthesis of various organic compounds. It serves as a valuable building block for the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Food Packaging Industry:
1,2-Diphenylcyclobutene is used as a potential print-related contaminant in food packaging. 1,2-Diphenylcyclobutene trans-1,2-Diphenylcyclobutane (D487505), which is synthesized from 1,2-Diphenylcyclobutene, is being investigated for its potential presence in food packaging materials. This is important for ensuring the safety and quality of food products.

Upstream product

• 58368-31-3 2-phenyl-2-(1-phenyl-cyclopropyl)-oxirane 
• 2548-47-2 2,3-diphenyl-1,3-butadiene 
• 495-71-6 phenacylacetophenone 
• 193211-89-1 (E)-1,2-diphenyl-1,4-diiodobut-1-ene 
• 593-60-2 Vinyl bromide 
• 17988-44-2 (cyclohex-1-en-1-ylethynyl)trimethylsilane 
• 6363-15-1 (1-phenylcyclopropyl)phenyl keton tosylhydrazone 
• 591-51-5 phenyllithium 
• 647028-03-3 1-phenylsulfonyl-2-phenyl-1-cyclobutene 
• 100-59-4 phenylmagnesium chloride 
• 74-85-1 ethene 
• 501-65-5 diphenyl acetylene 
• 5685-39-2 1-benzoyl-1-phenylcyclopropane 
• 451-40-1 phenyl benzyl ketone 

Downstream Products

• 7694-30-6 cis-1,2-diphenylcyclobutane 
• 64032-71-9 1,1',2,2'-Tetraphenylbicyclobutyl 
• 54393-31-6 2,5-Diphenyl-anti-tricyclo<4.3.0.0.^2.5>non-7-en 
• 118070-85-2 1,4-diphenyl-2,2,3,3-tetrachlorobicyclo<2.2.0>hexane 
• 113085-40-8 endo-2,2-dimethyl-1,4-diphenyl-3-(2-methyl-1-propenyl)bicyclo<2.2.0>hexane 
• 113036-77-4 exo-2,2-dimethyl-1,4-diphenyl-3-(2-methyl-1-propenyl)bicyclo<2.2.0>hexane 
• 4759-04-0 1,2,5,6-tetraphenyltricyclo<4.2.0.0^2,5>octane 
• 5685-39-2 1-benzoyl-1-phenylcyclopropane 
• 495-71-6 phenacylacetophenone 
• 222158-67-0 ((1S,2R,3S,4R)-3-Hydroxymethyl-1,4-diphenyl-bicyclo[2.2.0]hex-2-yl)-methanol 
• 13401-42-8 (1R,4S)-1,4-diphenylbutane-1,4-diol 
• 2085-90-7 (+/-)-1,4-diphenylbutane-1,4-diol 
• 5635-16-5 3,4-diphenyl-2(5H)-furanone 
• 6583-62-6 (2R,3S)-2,3-diphenylbutane-1,4-diol 

Relevant academic research and scientific papers

Addition of dichloro- and dibromocarbene to 1,2-diphenylcyclobutene

1,2-Diphenylcyclobutene (7) was reacted with dibromo- and dichlorocarbene, both generated via three different methods. 1,3-Diphenyl-2-halocyclopenta-1,3-dienes 12 were isolated which result from addition of the dihalocarbenes to the cyclobutene double bond of 7. A cationic cyclopropyl-allyl rearrangement (CCA) in gem-dihalobicyclopentanes 8 leads to 2,3-dihalocyclopentenes 9, which under the reaction conditions are dehydrohalogenated to 12. A second carbene addition and rearrangement afford aromatic compounds 11 and 16.

Tandem catalysis for asymmetric coupling of ethylene and enynes to functionalized cyclobutanes

Transformation of simple precursors into structurally complex cyclobutanes, present in many biologically important natural products and pharmaceuticals, is of considerable interest in medicinal chemistry. Starting from 1,3-enynes and ethylene, both exceptionally inexpensive starting materials, we report a cobalt-catalyzed route to vinylcyclobutenes, as well as the further enantioselective addition of ethylene to these products to form complex cyclobutanes with all-carbon quaternary centers. These reactions can proceed in discrete stages or in a tandem fashion to achieve three highly selective carbon-carbon bond formations in one pot using a single chiral cobalt catalyst.

Attempted preparation of 5,5-difluoro-1,4-diphenylbicyclo[2.1.0]pentane - Serendipitous synthesis of 1,3-difluoro-2,4-diphenylbenzene

Addition of difluorocarbene to 1,2-diphenylcyclobutene, using PhHgCF3, results in formation of 1,3-difluoro-2,4-diphenylbenzene. A mechanism for this reaction is proposed.

Molecular engineering of the glass transition: Glass-forming ability across a homologous series of cyclic stilbenes

We report on the glass-forming abilities of the homologous series 1,2-diphenylcyclo-butene, pentene, hexene and heptene-a series that retains the cis-phenyl configuration characteristic of the well-studied glass former, o-terphenyl. We find that the glass

Stereoselective Synthesis of anti-1,4-Diols by a BH3· THF-Mediated Rearrangement of 1,2-Disubstituted Cyclobutenes

A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1,2-disubstituted cyclobutenes, provides anti-1,4-diols with good-to-excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.

Synthesis of 1,3-Difluoroaromatics in One Pot by Addition of Difluorocarbene from Sodium Chlorodifluoroacetate to 1,2-Substituted Cyclobutenes

(Matrix Presented) The synthesis of 1,3-difluoro-2,4-diphenylbenzene has been accomplished in one step from 1,2-diphenylcyclobutene using the environmentally benign difluorocarbene precursor sodium chlorodifluoroacetate. In addition, the preparation of th

Electron-Transfer-Induced Rearrangements of Phenylated Tricyclo2,5>octane and 1,5-Cyclooctadiene

The hitherto unknown examples of cation radical isomerizations of tricyclo2,5>octane and 1,5-cyclooctadiene derivatives are reported.Photoreaction of 1,2,5,6-tetraphenyltricyclo2,5>octane (1) with 9,10-dicyanoanthrace

Magnesium- and Titanium-induced Reductive Coupling of Carbonyl Compounds: Efficient Syntheses of Pinacols and Alkenes

Finely dispersed magnesium on graphite was found to be a totally selective single-electron transfer reagent of general utility for the reduction of various kinds of carbonyl and dicarbonyl compounds to pinacols, a reaction quite compatible with a number of functional groups.Similarly, titanium on graphite proved to be a universally applicable reducing agent for the efficient conversion of pinacols, carbonyl and dicarbonyl compounds into alkenes and cycloalkenes respectively and for the cyclization of oxo alkanoates to enol ethers, facilitating and unifying the highly useful McMurry reaction.The practicability of the presently known carbonyl coupling methods is discussed in the light of these results.