Solid-phase supported nitrosocarbonyl intermediates: Old scope and new limitations in the organic synthesis

Nitrosocarbonyl intermediates on solid polystyrenic support are generated at room temperature by the
mild oxidation of resin-bound stable nitrile oxides. They undergo one-pot ene reactions with tetramethyl-
and trimethyl-ethylene and other highly substituted olefins. Less substituted ethylenes as well
as cyclohexene and cyclopentene are heavily disfavoured and nitrosocarbonyls on solid phase undergo
fast dimerization and/or decomposition pathways. These outcome strongly limit the SP applications in
organic synthesis, although applicable to structurally specific N-alkenyl hydroxamic acids.