Rearrangement of chlorinated β-diketone monomethyl enol ethers with sodium methoxide

✍ Scribed by Roland Verhé; Laurent De Buyck; Norbert De Kimpe; Antoine De Rooze; Niceas Schamp

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 374 KB
• Volume: 87
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19780870209

✦ Synopsis

Abstract

Reaction of the monomethyl enol ethers of 3‐chloro‐2,4‐pentanedione and 2‐chloro‐1‐phenyl‐1,3‐butanedione with sodium methoxide in methanol gave hydroxy enol ethers, respectively 3‐hydroxy‐2,4,4‐trimethoxy‐1‐pentene and 3‐hydroxy‐2,4,4‐trimethoxy‐4‐phenyl‐1‐butene. The reaction mechanism involving the formation and opening of an oxirane predominates the Favorskii‐rearrangement.