Bobbitt’s salt or 4-acetamido-2,2,6,6-tetramethylperidine-1-oxoammonium tetrafluoroborate,1, is a compound known for being more environmentally friendly than typical reagents used for oxidation. Unfortunately, it can only oxidize trifluoromethyl alcohols with difficulty. The preparation of trifluoromethyl ketones is of potential interest to the pharmaceutical industry, thus, we are seeking ways to enhance the oxidizing power of Bobbitt’s salt. This research project ultimately aims to synthesize two potential derivatives of interest, 2a and 2b, wherein a CH3 has been substituted with an electron-withdrawing group, and then test their oxidative efficacy. We are also interested in the precursor nitroxides as potential catalytic oxidants as well as novel spin labels. Five out of eight steps of our proposed syntheses have been successfully completed with reasonable yields. To date, we have been able to successfully synthesize 4a and 4b. Interestingly, the reductive amination to this step is highly selective to the isomer in which the NH2 and electron withdrawing group are trans to each other, as determined by NMR and verified by computational chemistry. We are currently working on the oxidation step from 4 to nitroxide 5 and are measuring oxidation potentials for 5.

Synthesis of alkyl fluoro derivatives of 4-acetamido-2,2,6,6-tetramethylperidine-1-oxoammonium tetrafluoroborate

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