Synthesis and spin trapping properties of polystyrene supported trifluoromethylated cyclic nitrones

Abstract

Polystyrene supported fluorinated cyclic nitrone spin-traps: Resin-2-HFDMPO (2-hydroxymethyl-2-methyl-5-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-1-oxide) and Resin-2-PFDMPO (2-(3-hydroxypropyl)-2-methyl-5-(trifluoromethyl)-3,4dihydro-2Hpyrrole 1-oxide) containing a trifluoromethyl pyrroline-N-oxide core were developed to detect free radicals under flow conditions. A continuous flow EPR technique was used to evaluate the spin trapping properties of these tethered nitrones. While both resins trapped radicals, polymer supported nitrone Resin-2-PFDMPO with a longer and more flexible linker showed a more information rich spectrum than Resin-2-HFDMPO.

3,4-Unsubstituted 2-tert-Butyl-pyrrolidine-1-oxyls with Hydrophilic Functional Groups in the Side Chains

“…Reductive cyclization of aliphatic γ-nitroketones is one of the most widely used methods of synthesis of pyrroline N -oxides [ 12 , 16 , 17 , 18 ], and reactions of the latter with organometallic reagents are commonly used for the preparation of pyrrolidine nitroxides [ 12 , 16 ]. Bulky substituents and functional groups can be introduced on the first step of this sequence of procedures.…”