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Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide

Author:
Krylov, Igor B., Paveliev, Stanislav A., Matveeva, Olesya K., Terent'ev, Alexander O.
Source:
Tetrahedron 2019 v.75 no.17 pp. 2529-2537
ISSN:
0040-4020
Subject:
ammonium nitrate, ceric ammonium nitrate, cerium, chemical reactions, chemical structure, iodine, organic compounds, solvents
Abstract:
Cerium(IV) ammonium nitrate was found to be a versatile reagent for the oxidative functionalization of styrenes using N-hydroxyphthalimide and iodine affording three different types of products with oxyphthalimide, nitrate and iodide groups. It was shown that reaction of styrenes with N-hydroxyphthalimide and cerium(IV) ammonium nitrate can be selectively directed to oxynitro-oxyphthalimides and dioxyphthalimides depending on the reaction conditions, in particular a solvent. Reaction of styrenes with iodine under the action of N-hydroxyphthalimide and cerium(IV) ammonium nitrate leads to the formation of iodo-oxyphthalimides.
Agid:
6350553