Diazirines, reaction with fluorid

Fluoro-3-pyridyl-3//-diazirines were prepared from the corresponding chlorodiazirines by exchange reaction with anhydrous tetrabutylammonium fluoride in dry dimethylformamide (25°C, 15-20 hours). " ... 

Alkoxy-3-chloro-3//-diazirines are obtained by the chlorination (aqueous sodium hypo-chlorite/dimethyl sulfoxide) of the corresponding amidines. They serve as precursors for the synthesis of 3-fluoro derivatives via the reaction with anhydrous tetrabutylammonium fluoride (for an improved procedure for the dehydration of commercial tetrabutylammonium fluoride trihydrate, see ref 26). This is a much simpler method than the earlier described preparation of 3-fluoro-3-methoxy-37/-diazirine involving the elemental fluorination reaction and a shatteringly explosive fluoronitrogen intermediate. 

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