113111-23-2

Basic information

• Product Name: Thiophene, tetraphenyl-, 1-oxide
• CAS NO: 113111-23-2
• Molecular Formula: C28H20OS
• Molecular Weight: 404.532
• Mol File: 113111-23-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Thiophene, tetraphenyl-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, tetraphenyl-, 1-oxide(113111-23-2)
• EPA Substance Registry System: Thiophene, tetraphenyl-, 1-oxide(113111-23-2)

Safety Data

• Hazardous Substances Data: 113111-23-2(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.