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Elementalfluorine. Part 14.1 Electrophilic fluorination and nitrogen functionalisation of hydrocarbons

Selective fluorination of a range of hydrocarbons was achieved by reaction with either elemental fluorine or Selectfluor, an electrophilic fluorinating reagent of the N-F class. An electrophilic mechanism is envisaged. On prolonged reaction, the strongly acidic reaction medium that is formed upon substitution of hydrogen by fluorine when Selectfluor is used as the fluorinating reagent, promotes loss of fluoride from the initial fluorinated product. Trapping of the subsequent carbocation by the acetonitrile solvent in a Ritter type process gives overall nitrogen functionalisation of hydrocarbons. Amidation of hydrocarbons could also be achieved in a one-stage process by reaction of the hydrocarbon with fluorine and a Lewis acid, such as boron trifluoride-diethyl ether, in acetonitrile.

Electrophilic fluorination at saturated sites

Transformation of carbon-hydrogen bonds to carbonfluorine bonds at saturated secondary and tertiary carbon sites by electrophilic aliphatic substitution processes is possible using either elemental fluorine or fluorinating reagents of the N-F class.

Activating Unreactive Sites of Organic Molecules Using Elemental Fluorine

Electrophilic substitution reactions on saturated carbons are extremely rare.Elemental fluorine, however, uses this pathway to replace tertiary unactivated hydrogens with great regio- and stereoselectivity, resulting in a full retention of configuration.I

ACTIVATION OF TERTIARY PARAFFINS BY ELEMENTAL FLUORINE

Elemental fluorine was found to substitute, in a regio and stereospecific way, tertiary unactivated hydrogens in alkanes - the most unreactive family of organic compounds.