A novel synthesis of monosubstituted sulfines via an unusual β-elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides

✍ Scribed by Samuel Braverman; Dan Grinstein; Hugo E. Gottlieb

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 344 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)76009-6

✦ Synopsis

A new method for the synrhess of thioakiehyde S-oxides by base-induced elimination of chloroform from allyiic and benzylic trichloromethyl sulfoxides is described. The reaction proceed smoothly under mild conditions. A mechanic for this remarkable sulfine synthesis and apparently unprecedented j%elimination of chloroform is presented

During studies on the rearrangement of ally1 trichloromethanesulfinates to ally1 trichloromethyl sulfones, we found that these sulfones, unlike the corresponding aryl sulfones, undergo an unusually fast isomerization to vinylic sulfones even in the presence of weak bases such as triethylamine or 2,6-lutidine.2 This reaction is not only of mechanistic interest but also of synthetic utility due to the growing importance of vinyl sulfones in organic synthesis in recent years3 H H H 1a.b 2a.b