ChemInform Abstract: Unexpected Enolization of 2-Phenyl-3-piperidone Derivatives.

✍ Scribed by V. DALEY; C. CAVE; J. D'ANGELO

• Book ID: 101878098
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 28 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199907153

✦ Synopsis

Unexpected Enolization of 2-Phenyl-3-piperidone Derivatives.

-Alkylation of piperidone (I) furnishes the 4,4-dialkylated derivatives (III) and (V). This unexpected enolization towards the less substituted enolate is rationalized by consideration of the appreciable steric strain which would exist in the more substituted form. Interestingly, it is not possible to isolate a monoalkylation product even in the presence of 1 equiv. alkylating reagent. -