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Thiophene sulfoximides: 2,4- and 3,4-di-tert-butyl-1-imino-1,1-dihydrothiophene 1-oxides

✍ Scribed by Juzo Nakayama; Yuki Sano; Yoshiaki Sugihara; Akihiko Ishii

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
226 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Preparation of sulfoximide derivatives of monocyclic thiophenes is reported.

Treatment of 2,4-di-tert-butylthiophene l-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-I -[(p-toluenesulfonyl)imino]-1, l-dihydrothiophene i-oxide (8) in 81% yield. Hydrolysis of 8 with concentrated H2SO4 at room temperature furnished 2,4-ditert-butyl-I -imino-1,1-dihydrothiophene l-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.

📜 SIMILAR VOLUMES

Cyclische Sulfoximide, VI. 3-Imino-3H-1λ
Cyclische Sulfoximide, VI. 3-Imino-3H-1λ4,2-benzisothiazol-1-oxide
✍ Stoss, Peter ;Satzinger, Gerhard 📂 Article 📅 1975 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 318 KB 👁 1 views

## Abstract 2‐Sulfinylbenzamide **3** reagieren mit Stickstoffwasserstoffsäure zu 3‐Imino‐3__H__‐1λ^4^,2‐benzisothiazol‐1‐oxiden **4**, die durch Substitution am Imin‐Stickstoff die Derivate **9**–**12** liefern.

1-imino and 1,1-diimino derivatives of 3
1-imino and 1,1-diimino derivatives of 3,4-di-tert-butylthiophene
✍ Takashi Otani; Yoshiaki Sugihara; Akihiko Ishii; Juzo Nakayama 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 238 KB

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 ), and 1-(p-tolylsulfonyl)-3,4-di-tertbutylpyrrole (5) as the principal products. The use of 2 in a large excess gave 3 in a bet