ABSTRACT
Selective fluorination of adamantanes was achieved by the electrochemical fluorination method, using Et 3N-5HF as electrolyte and a fluorine source. Mono-, di-, tri-, and tetrafluoroadamantanes were selectively prepared from adamantanes by controlling the oxidation potential, and the fluorine atoms were introduced selectively at the tertiary carbons. Adamantanes that have functional groups such as ester, cyano, and acetoxymethyl were also fluorinated selectively.
Subject(s)
Adamantane/chemistry , Electrochemistry/methods , Fluorine/chemistry , Magnetic Resonance Spectroscopy , Oxidation-Reduction , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, InfraredABSTRACT
Selective monofluorination of 1,2- and 1,3-diols was achieved by reaction with DFMBA. The method is applicable for the synthesis of optically-active fluorohydrin derivatives.
ABSTRACT
[reaction: see text] In the reaction of p-chlorophenyl alkyl sulfides with IF(5), polyfluorination reaction took place on the alkyl chain with the migration of the arylthio group. Consequently, p-chlorophenyl polyfluoroalkyl sulfides, having 3-7 fluorine atoms depending on alkyl chain length, could be obtained selectively.
