Tetrahedron p. 5809 - 5820 (1999)
Update date:2022-07-29
Topics:
Coustard, Jean-Marie
In triflic acid, 1-amino-2-nitroene derivatives undergo a C,O- diprotonation followed by the loss of (protonated) water, to form the >C=N < conjugated hydroxynitrilium ions that can react, in a competitive way, either with TfO or with added C6H6. The resulting phenylated dications can be selectively reduced by NaBH4 at the iminium bond moiety. A protonated nitroso derivative was also isolated as its triflate salt. Structure, reactivity and mechanism of these reactions are discussed.
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