Fluorine diazo group replacement with

It has been demonstrated that the presence of chlorine or bromine in the nucleus facilitates replacement of the diazo group by hydrogen little or no ether formation occurs.26 Apparently iodine also favors the redudng action of alcohols, but this point has not been investigated carefully.26 27 No attempts to deaminate fluorinated amines are recorded. Representative of the effitiency with which ethanol reduces diazonium salts derived from halogenated amines are the deaminations of m-chloroaniline 26 (87% yield), of 2-bromo-4-methylaniline 28 (67% yield), of 2,4,6-tribfomoaniline 29 (ca. 80% yield), and of 2-carboxy-4-iodoaniline30 (ca. 45% yield) in the biphenyl series the deamination of VIII in 53% yield 31 may be dted. 

If the diazonium ion is heated in the presence of tetrafluoroborate ion, the diazo group is replaced with a fluorine ... 

Replacement of Diazo Sulfide Groups with Fluorine in the Silver(l) Ion Promoted Acid Decomposition of Aryl Diazo Sulfides... 

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