A Novel Electrophilic Methoxylation (with a Little Help from F2)

Shlomo Rozen*, Eyal Mishani, Moshe Kol

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

Methyl hypofluorite, MeOF, easily made from MeOH and F2, proved to be an excellent source for the novel electrophilic methoxylium ion “MeO+”. MeOF was reacted with the enol forms of carbonyls, producing in good to excellent yields the corresponding α-methoxy carbonyl derivatives. It was found that the methoxylation is best carried out on methyl enol ethers. Silyl enol ethers and enol acetates were also tested but with limited success. The reaction proceeds through an addition elimination mechanism.

Original languageEnglish
Pages (from-to)7643-7645
Number of pages3
JournalJournal of the American Chemical Society
Volume114
Issue number20
DOIs
StatePublished - 1 Sep 1992

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