Add time:07/11/2019 Source:sciencedirect.com
Preparation of sulfoximide derivatives of monocyclic thiophenes is reported. Treatment of 2,4-di-tert-butylthiophene 1-oxide (4) with N-[(p-toluenesulfonyl)imino]-phenyliodinane (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 (8) in 81% yield. Hydrolysis of 8 with concentrated H2SO4 at room temperature furnished 2,4-di-tert-butyl-1-imino-1,1-dihydrothiophene 1-oxide (9) in 89% yield. Optical resolution of a pair of enantiomers of 9 was performed by HPLC on a chiral column and their absolute configuration was determined by an X-ray crystallographic analysis.
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