Organic Letters p. 1957 - 1959 (1999)
Update date:2022-08-03
Topics:
Song, Fenhong
St. Hilaire, Valentine R.
White, Emil H.
(matrix presented) The protonation of heterocyclic diazotates (attachment adjacent to a nitrogen atom) yields ring-centered heterocyclic carbocations that are highly reactive. The carbocations were found to alkylate aromatic and heterocyclic compounds, such as benzene, N-methylpyrrole, and 2-aminopyridine, in reactions that are synthetically useful. This carbocation involvement may serve as a paradigm for the cross-linking of DNA by nitrous acid and the anticancer activity of heterocyclic diazotates.
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