The Chemistry of Short-Lived α-Fluorocarbocations

Shlomo Rozen, Inna Vints, Ana Lerner, Oded Hod, Edward N. Brothers, Salvador Moncho

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


The present study of the chemistry of short-lived α-fluorocarbocations reveals that even inactive methyl carbons can serve as nucleophiles, attacking a cationic center. This, in turn, facilitates the synthesis of a cyclopropane ring in certain triterpene backbones. We report the synthesis of compounds similar to 2, containing a bridgehead cyclopropane, and compounds of type 3 with an 11 membered bicyclic ring consisting of two bridgehead double bonds (anti-Bredt) within a triterpene skeleton. The synthesis involves three unconventional chemical processes: (a) a methyl group serving as a nucleophile; (b) the unexpected and unprecedented synthesis of a strained system in the absence of an external neighboring trigger; and (c) the formation of an 11-membered bicyclic diene ring within a triterpenoid skeleton. An α-fluorocarbocation mechanism is proposed and supported by density functional theory calculations.

Original languageEnglish
Pages (from-to)3882-3889
Number of pages8
JournalJournal of Organic Chemistry
Issue number5
StatePublished - 5 Mar 2021

ASJC Scopus subject areas

  • Organic Chemistry


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