113111-23-2

Upstream product

• 501-65-5 diphenyl acetylene 
• 1884-68-0 tetraphenylthiophene 
• 7719-09-7 thionyl chloride 
• 53433-58-2 1,1-bis(cyclopentadienyl)zircona-2,3,4,5-tetraphenylcyclopentadiene 

Downstream Products

• 96972-18-8 1,2-dibenzoyl-3,4,5,6-tetraphenylbenzene 
• 1113056-88-4 C₃₆H₂₆O₃S₂ 
• 751-38-2 1,2,3,4-tetraphenylnaphthalene 

Relevant academic research and scientific papers

Trisulfur Radical Anion (S3?-) Involved [1 + 2 + 2] and [1 + 3 + 1] Cycloaddition with Aromatic Alkynes: Synthesis of Tetraphenylthiophene and 2-Benzylidenetetrahydrothiophene Derivatives

S3?--mediated [1 + 2 + 2] and [1 + 3 + 1] cycloaddition reactions of aromatic alkynes to give tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives via two C-S bond formations are developed. These two protocols provide new, simple, and straightforward strategies to construct tetraphenylthiophene and 2-benzylidenetetrahydrothiophene derivatives under transition-metal-free conditions. This study also expands the application of S3?- in organic reactions.

Thiophene S-Oxides: Convenient Preparation, First Complete Structural Characterization and Unexpected Dimerization of One of Them, 2,5-Diphenylthiophene-1-oxide

Oxidation of 2,5-disubstituted thiophenes and benzothiophenes by H2O2 in CF3CO2H-CH2Cl2 appears a convenient method to access the corresponding reactive sulfoxides; it is used to prepare 2,5-diphenylthiophene-1-oxide, which is the first thiophene oxide to

Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne

Thiophenes have been treated with alkynes in the presence of m-chloroperoxybenzoic acid to give substituted arenes as cycloadducts. Alternatively, thiophene S-oxides have been prepared by oxidation from thiophenes and have been subjected to cycloaddition with alkynes in a subsequent step. The outcome of the reaction is dependent on the steric demand of the thiophene S-oxide. Some thiophene S-oxides can be reacted at temperatures as high as 140°C without decomposition. Thiophenes as deoxygenated products are the main by-products. Reactions of thiophene S-oxides with allenes give in part thiabicyclo[2.2.1]heptene S-oxides of type 12a and 13 along with aromatized products. Thiophene S-oxides also cycloadd to benzyne.

Metallacycle transfer from zirconium to main group elements: A versatile synthesis of heterocycles

The reaction of zirconium metallacycles is used to produce a variety of main group heterocycles including borole Diels-Alder dimers, galloles, indacyclopentadienes, siloles, germoles, stannoles, phospholes, arsoles, stiboles, bismoles, thiophenes, selenophenes, dihydrothiophenes, dihydroselenophenes, tetrahydrothiophenes, tetrahydro-selenophenes, stannacyclopentanes, phospholenes, and isothiazoles. An X-ray crytallographic study of the borole DielsAlder dimer of 1-phenyl-2,3,4,5-tetramethylborole is discussed and compared with the structure of 7-norbornenyl carbenium ions. The scope and potential for this metallacycle transfer reaction are delineated.

Tetraphenylzirkonacyclopentadien-Derivate als Synthone fuer Tetraphenylthiophenmonoxid und substituierte Germanole

Improved syntheses for the five-membered heterocycles 2,3,4,5-tetraphenylthiophene-1-monoxide (1), 1,1-dichloro-2,3,4,5-tetraphenylgermole (3) and 1,1-dimethyl-2,3,4,5-tetraphenylgermole (4) are reported.They make use of bis(η5-cyclopentadienyl)-2,3,4,5-tetraphenyl-1-zirconacyclopentadiene (2), easily prepared in a one-step reaction from Cp2ZrCl2, n-BuLi and diphenylethyne.Further reaction of 2 with SOCl2, GeCl4 or Me2GeCl2 yields the desired products and allows recovery of Cp2ZrCl2.Crystal structure analyses of 1 and 4 demonstrate folded five-membered rings with a diene system.Starting from 3 the following derivatives have been synthesized: Ph4C4Ge(CCR)2 (R = H, t-Bu, Ph), Ph4C4GeCl (10) and Ph4C4GeCl.Moreover spectral data (IR, 1H NMR, 13C NMR) of all compounds and the crystal structure of 10 are reported.