130826-16-3

Upstream product

• 116375-45-2 3,4-di-tert-butyl-thiophene 1,1-dioxide 
• 321124-82-7 3,4-di-tert-butyl-1λ⁴-thiophen-1-ylideneamine 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 118888-09-8 3,4-Di-tert-butylthiophene S-oxide 
• 98-59-9 p-toluenesulfonyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 22808-03-3 3,4-di-tert-butylthiophene 
• 243123-91-3 3,4-di-tert-butyl-1-[(p-tolylsulfonyl)imino]-1,1-dihydrothiophene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 941-55-9 4-toluenesulfonyl azide 

Relevant academic research and scientific papers

1-Imino and 1,1-diimino derivatives of 3,4-di-tert-butylthiophene

The reaction of 3,4-di-tert-butylthiophene (2) with N-[(p- tolylsulfonyl)imino]phenyliodinane (TsN=IPh) in the presence of Cu(MeCN)4PF6 in MeCN at room temperature provided 3,4-di-tert-butyl-1-[(p- tolylsulfonyl) imino]-1,1-dihydroth

Syntheses and structures of sulfilimine, sulfone diimine, and sulfoximine derivatives of a monocyclic thiophene, 3,4-di-tert-butylthiophene

The reaction of 3,4-di-tert-butylthiophene (6a) with N-[(p-tolylsulfonyl)imino]-phenyliodinane (TsN=IPh) in the presence of Cu(MeCN)4PF6 in MeCN at room temperature provided 3,4-di-tert-butyl-1-[(p-tolylsulfonyl)imino]-1,1-dihydrothiophene (3b), 3,4-di-tert-butyl-1,1-bis[(p-tolylsulfonyl)imino]-1,1-dihydrothiophene (5a), and 1-(p-tolylstdfonyl)-3,4-di-tert-butylpyrrole (7a) as the principal products. The use of 20 molar amounts of 6a gave 3b in an increased yield of 61%. Treatment of 3,4-di-tert-butylthiophene 1-oxide (1a) with (CF3CO)2O or (CF3SO2)2O, followed by reactions with RSO2NH2, ROC(=O)NH2, or RCONH2, furnished a series of S-imino derivatives (3b,c,e-h) of 6a, which carry an electron-withdrawing substituent on the imino nitrogen atom. Treatment of the S-imino derivative 3f (substituent on the nitrogen atom = CO21Bu) with CF3CO2H gave an aminosulfonium salt (13), whose deprotonation led to the parent N-unsubstituted 1-imide derivative (3n). Treatment of 2,4-di-tert-butylthiophene 1-oxide (1b) with TsN = IPh in the presence of Cu(MeCN)4PF6, in MeCN at room temperature provided 2,4-di-tert-butyl-1-[(p-toluenesulfonyl)imino]-1,1-dihydrothiophene 1-oxide (4e) in 81% yield. Hydrolysis of 4e by concentrated H2SO4 at room temperature furnished 2,4-di-tert-butyl-1-imino-1,1-dihydrothiophene 1-oxide (4f) in 89% yield. A pair of enantiomers of 4f were separated by high-performance liquid chromatography (HPLC) on a chiral column, and their absolute configurations were determined by an X-ray crystallographic analysis. Structures of sulfilimine, sulfone diimine, and sulfoximine derivatives of monocyclic thiophenes, obtained in these ways, are discussed based on spectroscopies (IR and 1H and 13C NMR) and X-ray crystallographic analyses.

Synthesis and characterization of 3,4-Di-t-butylfuran, pyrrole, and selenophene

3,4-Di-t-butylfuran (1), pyrrole (2), and selenophene (4) were first synthesized using 3,4-di-t-butylthiophene (3) as the starting material and these overcrowded five-membered hetarenes including 3 were characterized by NMR and MMP2 calculations.