Tert-Butyl Hypofluorite - An Electrophilic tert-Butoxylation Agent

Iris Ben-David, Eyal Mishani, Shlomo Rozen

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)4632-4635
Number of pages4
JournalJournal of Organic Chemistry
Volume63
Issue number14
DOIs
StatePublished - 10 Jul 1998

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