Journal of the American Chemical Society p. 5657 - 5660 (1983)
Update date:2022-08-12
Topics:
Mertens, Alfred
Lammerstma, Koop
Arvanaghi, Massoud
Olah, George A.
Protonation of hydrazoic acid and alkyl azides with FSO3/SbF5, HF/SbF5, or HF/BF3 results in the formation of stable aminodiazonium ions as shown by 1H, 13C, and 15N NMR spectroscopic studies.Molecular orbital calculations of the thermodynamics of the protonation of hydrazoic acid also support preferential formation of the aminodiazonium ion.The aminodiazonium ion was also prepared in situ from NaN3/AlCl3/HCl or (CH3)3SiN3/AlCl3/HCl <(CH3)3SiN3/HF/BF3>.Aminodiazonium salts were found to affect electrophilic amination of aromatics in high yields, with generally high regioselectivity and low substrate selectivity.
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