Reactions at a nitrogen centre

Although the most extensively recorded aspect of phosgene chemistry is its interaction with compounds at a nitrogen centre, only three reactions of carbonyl chloride fluoride with amines have been reported. No reports have appeared concerning the reactions of COCIF with tertiary amines, amino acids, hydrazine derivatives, imino compounds or nitrogen-containing heterocycles, to name but a few unstudied reagents. 

A vigorous reaction is observed between an ethereal solution of diethylamine and COCIF even at -78 C [589]. The product consisted of a mixture of diethylcarbamyl fluoride and diethylamine hydrochloride, which was separated by distillation  

N-methylaniline also was found to react at low temperature with COCIF [589], to give a high yield of the corresponding carbamyl fluoride (16.2)  

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