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Oxidation of N , N ‐Disubstituted Hydroxylamines to Nitrones with Hydrogen Peroxide Catalyzed by Polymer‐Supported Methylrhenium Trioxide Systems
Author(s) -
Saladino Raffaele,
Neri Veronica,
Cardona Francesca,
Goti Andrea
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303223
Subject(s) - chemistry , hydrogen peroxide , catalysis , polystyrene , trioxide , organic chemistry , environmentally friendly , polymer , combinatorial chemistry , polymer chemistry , ecology , sulfur , biology
Poly(4‐vinylpyridine)/methylrhenium trioxide (MTO) compounds IIII and microencapsulated polystyrene/MTO systems IVV are efficient catalysts for the oxidation of secondary hydroxylamines to the corresponding nitrones with H 2 O 2 . Complete conversions of substrates and quantitative yields of products are obtained under environmentally friendly experimental conditions and with the use of simple work‐up procedures. Symmetrically substituted hydroxylamines, and non‐symmetrical 3‐substituted and 2‐substituted hydroxypyrrolidines, precursors of nitrones applied in the synthesis of alkaloids and biologically active congeners, have been considered as substrates. The heterogeneous catalysts are stable under the reaction conditions and can be recovered and recycled for at least five times without any appreciable loss in efficiency.