Isomérisation d'époxydes d'acétates d'énols en série pinanique
Keyword(s):
The isomerization of enol acetate epoxides by zinc bromide leads to ketoacetates with retention of configuration. Thermal isomerization yields a ketoacetate with inversion of the configuration by a concerted mechanism if the oxirane does not contain a hydrogen atom. In the case of an oxirane containing hydrogen, an 'acid' type mechanism competes favorably with the concerted mechanism; the former yields a ketoacetate with retention of configuration. The isomer in which the configuration is retained is not the most stable. [Journal translation]