The Pummerer-like reaction of 2,5-bis(trimethylsilyl)thiophene S-oxide with trifluoroacetic anhydride: intermediary formation of sulfurane [10-S-4(C2O2)] (λ4-sulfane)

✍ Scribed by Soichi Sato; Shao-Zhong Zhang; Naomichi Furukawa

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 166 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.1066

✦ Synopsis

Abstract

On treatment of a 2,5‐bissilylsubstituted thiophene S‐oxide or dibenzothiophene S‐oxide with trifluoroacetic anhydride, the equillibria between the corresponding substrates and hypervalent sulfur compounds (sulfurane or λ^4^‐sulfane) have now been first detected by low temperature NMR experiments. By elevating the temperature to room temperature, in the case of the thiophene S‐oxide, the sulfurane detected was converted to 3‐thiolene‐2‐one quantitatively via a Pummerer‐like reaction. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:444–450, 2001