36336-08-0Relevant articles and documents
The Chemistry of Methyl Hypofluorite: Its Reactions with Various Unsaturated Centers
Rozen, Shlomo,Mishani, Eyal,Kol, Moshe,Ben-David, Iris
, p. 4281 - 4284 (1994)
Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized.Passing F2 through a solution of methanol in MeCN or PrCN resulted in this successful preparation.MeOF is an unique reagent, since it generates the novel electrophilic methoxylium moiety in contrast to the much more common methoxide group.This hypofluorite was reacted with several types of olefins including benzylic, cyclic, bicyclic, straight chain, and steroidal ones.In most cases the regioselectivity is very good, reflecting the unique polarization of the reagent: MeOδ(+)Fδ(-).The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.
A novel electrophilic methoxylation (with a little help from F2)
Rozen, Shlomo,Mishani, Eyal,Kol, Moshe
, p. 7643 - 7645 (2007/10/02)
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.