Stereochemistry of acetolysis of 2-octyl p-toluenesulfonate

✍ Scribed by A. Streitwieser Jr.; T.D. Walsh

• Book ID: 104241766
• Publisher: Elsevier Science
• Year: 1963
• Tongue: French
• Weight: 331 KB
• Volume: 4
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90571-4

✦ Synopsis

SOLVOLYSES of secondary alkyl systems frequently fall in the "borderline" region of solvolytic behavior in which controversy about detailed mechanism still exists.

Especially interesting is the reaction of simple secondary alkyl sulfonates in acetic acid in which various criteria suggest a limiting mechanism. 4

Surprisingly, the only published stereochemical studies of such a system come from Kenyon's group5 who obtained only the qualitative result of substantial net inversion of configuration in the reaction of 2-butyl or 2-octyl p-toluenesulfonate with acetic acid. We report here a more detailed study of the latter system which has revealed unexpected facets of this reaction.