UNEXPECTED ENOLIZATION OF 2-PHENYL-3-PIPERIDONE DERIVATIVES

Authors
DALEY V CAVE C DANGELO J
Citation
V. Daley et al., UNEXPECTED ENOLIZATION OF 2-PHENYL-3-PIPERIDONE DERIVATIVES, Heterocycles, 48(10), 1998, pp. 2157-2162
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
10
Year of publication
1998
Pages
2157 - 2162
Database
ISI
SICI code
0385-5414(1998)48:10<2157:UEO2D>2.0.ZU;2-8
Abstract
Alkylation of 2-phenyl-3-piperidone (17) with methyl iodide or methyl acrylate furnished the 4,4-dialkylated derivatives (18) or (19), respe ctively. This unexpected enolization towards the less substituted form can be interpreted considering the appreciable steric strain which wo uld exist in the more substituted enolate (21).