210540-78-6Relevant articles and documents
Tert-Butyl Hypofluorite - An Electrophilic tert-Butoxylation Agent
Ben-David, Iris,Mishani, Eyal,Rozen, Shlomo
, p. 4632 - 4635 (1998)
tert-Butyl hypofluorite, t-BuOF, easily synthesized from Z-BuOH and F2, is a unique source of the novel electrophilic tert-butoxylium moiety t-BuO+. It was added to several benzylic double bonds to form vicinal fluoro-tert-butoxide derivatives. Not surprisingly, this bulky reagent is quite sensitive to steric hindrance. The process is electrophilic in nature, but since the reaction is relatively slow (20-60 min) formation of various radical species can take place, forming eventually several distinct byproducts. t-BuOF was also reacted with a number of enols, producing the corresponding α-tert-butoxy ketone derivatives in moderate to good yields. The best results were obtained with benzylic enol derivatives.