N-nitration of salts of primary nitramines by nitryl fluoride
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A method has been developed for the N-nitration of the anions of primary nitramines with nitryl fluoride to N,N-dinitramines.
Bulky tetraalkylammonium cations in nitramine salts direct the attack of nitryl fluoride on the nucleophilic amine center of the ion, whereas the harder metal cations favor O-nitration.
In the nitration of nitramine anions by nitronium tetrafluoroborate, the opposite effect is observed with respect to the influence of the salt cation on the outcome of the reaction, i.e., bulky, soft cations favor O-nitration.
KeywordsFluoride Opposite Effect Metal Cation Nitration Tetrafluoroborate
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