1487-12-3

Usage

Class of compound

Polyphenyls (compounds containing a chain of benzene rings connected by single bonds)

Molecular structure

Symmetric molecule with four phenyl (C6H5) groups attached to the four carbon atoms of a benzene ring

Usage in research

Model compound for studying the reactivity and properties of polyphenyl compounds in organic chemistry

Applications in material science

Building block for designing molecular devices and materials with specific electronic, optical, and structural properties

Upstream product

• 6971-41-1 3,4,5,6-tetraphenyl-1,2-dihydro-o-phthalic anhydride 
• 113451-37-9 C₇₂H₅₀O₄ 
• 959-28-4 1,4-diphenylbut-2-ene-1,4-dione 
• 109-99-9 tetrahydrofuran 
• 501-65-5 diphenyl acetylene 
• 139259-29-3 1,12,13,14,15,15-hexachloropentacyclo<10.2.1.1^5,8.0^2,11.0^4,9>hexadeca-2(11),6,13-triene 
• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 

Relevant academic research and scientific papers

Sequential Cycloaddition-Cycloreversion-Cycloaddition-Cope Rearrangement with an Annelated Norbornadiene and Electrophlic Dienes. Unusual 2s + ?2a + ?2a>Transformation of a Pentacyclo-7,10.04,13.06,11>octadeca-3,8,14,17-tetraene.

Hexachloronorbornadiene efficiently forms a 1:1 adduct 3 with 5,6-bismethylenenorbornene.Adduct 3 on reaction with 1,2,3,4-tetrachlorothiophene dioxide (TCTD) under mild conditions gives an SO2 bridged adduct,which loses SO2, the product cycloreverting to give 1,2,3,4-tetrachlorobenzene and an annelated cyclopentadiene 8; 8 reacts further with TCTD to give, in 1:1 ratio, two compounds (14 and 15) shown by mass, 13C and 1H NMR spectroscopy and single crystal X-ray structure determination to be the stereoisomeric products of a rare type of specific diene capture by TCTD.E vidence is presented that this result (and analogous examples) is best understood in terms of ''normal'' ? cycloadditions to 8 as dienophile towards electron-deficient TCTD, followed by rapid Cope rearrangement of the SO2-bridged intermediate adducts to give the observed products.At low temperatures adduct 3 behaves as expected towards electron-deficient diene tetracyclone; the ? cycloadduct decarbonylates on mild thermolysis, concomitant cycloreversion also giving diene 8.At much higher temperatures in the presence of excess tetracyclone, diene 8 likewise behaves as dienophile; the carbonyl-bridged major cycloadduct decarbonylates to give an intermediate which undergoes an unusual thermally-allowed 2s + ?2a + ?2a> 1,3-shift/cycloaddition, delivering a symmetrical cage-like structure 24, as indicated by mass and 13C and 1H NMR spectroscopy.

Photochemical Studies. On the Photofragmentation of Substituted 1,2-Dihydrophthalic Anhydrides

The irradiation-induced transformations of 4,5-diphenyl-1,2-dihydrophthalic anhydride (2b) as well as those of the 3,6-dimethyl-4,5-diphenyl and 3,4,5,6-tetraphenyl derivatives (2c,d) are elaborated.All undergo photofragmentation, viz., CO + CO2 ejection to give aromatic hydrocarbons, while only 2b also closes electrocyclically to the bicyclohex-5-ene product 5.The quantum yields for fragmentation are indicative in this respect.The rearrangement accompanying the fragmentation of 2d to give 1,2,3,5-tetraphenylbenzene (11) was shown to occur via a triplet excited state, populated by benzene sensitization.