547741-33-3

Upstream product

• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 547741-31-1 (1S,2R,5S)-2,5-Dibromo-3,4-di-tert-butyl-2,5-dihydro-thiophene 1-oxide 
• 226927-24-8 3,4-di-tert-butyl-1-[(p-toluenesulfonyl)imino]-1,1-dihydrothiophene 1-oxide 
• 118888-09-8 3,4-Di-tert-butylthiophene S-oxide 

Relevant academic research and scientific papers

Regio- and stereo-chemistry of addition of molecular bromine to s-oxidized derivatives of 3,4-di-t-butylthiophene: Exclusive 1,4-cis-additions

Bromine added to the 1-oxide, 1,1-dioxide, and sulfoximide derivatives of 3,4-di-t-butylthiophene exclusively in a 1,4-cis-addition mode. Thus, bromine added to 3,4-di-t-butylthiophene 1-oxide at room temperature in CH2Cl2 to give the 1,4-cis-adducts exclusively. The adducts are composed of two compounds in the ratio 57:43, where the major one is the anti-adduct respective to the S=O bond and the minor one is the syn-adduct. Addition of bromine to 3,4-di-t-butylthiophene 1,1-dioxide gave the 1,4-cis-adduct as the sole product. Addition of bromine to the N-tosyl substituted sulfoximide derivative of 3,4-di-t-butylthiophene afforded the single 1,4-cis-adduct in which two bromine atoms are anti to the N-tosyl group. Bromine added to the N-unsubstituted sulfoximide derivative of 3,4-di-t-butylthiophene to produce the 1,4-cis-addition products exclusively, which are a 67:33 mixture of the anti- and syn-adducts to the S=O bond.