The parent nitrenium ion generated from N-aminopyridinium, S-aminosulphonium, or N-aminobipyridinium salts interacts with both the unshared electron pair of the heteroatom of pyridine, sulphide, or bipyridyl and the gegen anion by hydrogen bonding; the singlet nitrenium ion is stabilised by this interaction, and the stabilised singlet state undergoes fast singlet → triplet conversion in the presence of molecular oxygen or chlorine.
H. Takeuchi, S. Hayakawa and H. Murai, J. Chem. Soc., Chem. Commun., 1988, 1287 DOI: 10.1039/C39880001287
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