Stereochemistry of α-sulfonyl carbanions

✍ Scribed by E.J. Corey; Horst König; Thomas H. Lowry

• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 303 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70505-3

✦ Synopsis

A PREVIOUS note from this laboratory has reported 2-octyl sulfone undergoes base-cata?yzed exchange the finding that phenyl of a-hydrogen in deuterated aqueous ethanol at a rate which is much faster than the rate of racemization.1'2 It can be conc1uded that a least 98 per cent of the benzenesulfonyl methyl n-hexyl carbanions produced in these experiments are optically active and that asymmetry can be maintained until subsequent protonation.