1.
J Org Chem
; 71(22): 8647-50, 2006 Oct 27.
Artigo
em Inglês
| MEDLINE
| ID: mdl-17064050
RESUMO
Conversion of an alpha,alpha-dichloroester to the corresponding alpha-keto acid was unexpectedly complicated by a novel 1,4-homofragmentation. Investigation of the kinetics of this reaction revealed a mechanism involving an alpha-lactone intermediate, which can lead to both the desired alpha-keto acid and the 1,4-homofragmentation, with the product distribution being dependent upon reaction conditions. This information allowed development of a process that affords the alpha-keto acid exclusively and should be generally applicable to the preparation of alpha-keto acids from alpha,alpha-dichloroesters or acids.