Isomerization of enol esters derived from 2-acyl-1,3-cyclohexanediones: mechanism and driving force

✍ Scribed by Hun-Ge Liu; Chung-Shieh Wu; Jen-Fei Wang; Ding-Yah Yang

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 217 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00554-9

✦ Synopsis

A series of 2-acyl-1,3-cyclohexanediones were prepared and isomerization mechanisms of the corresponding enol esters were investigated. The driving force for this migration is likely that the intrinsic electrostatic repulsion between the 2-acyl oxygen atom and the two 1,3-diketone oxygens caused deformation of enol esters from planarity and resulted in their high susceptibility to enolization and subsequent isomerization.