The oxoammonium salt 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate, or Bobbitt’s salt, has been emerging as a green oxidizing agent. However, this salt does not readily oxidize alcohols with electron withdrawing groups, such as α-trifluoromethyl alcohols, to the corresponding ketones. Therefore, this project outlines a synthesis of a modified Bobbitt’s salt with an electron withdrawing group replacing one of the methyl groups. It is hoped that this modified oxoammonium salt will have an enhanced the oxidizing capability, thereby facilitating reaction of difficult-to-oxidize alcohols. This transformation is important because it can provide an easy way to obtain trifluoromethylated ketones. These ketones have many uses in organic chemistry as they can be reacted with Grignard reagents to make carbon-carbon bonds, and are also known enzyme inhibitors. Therefore, the purpose of this project is to develop the synthesis of an electron withdrawing Bobbitt salt to be used as a potential green oxidant for electron withdrawing alcohols.

Synthesis of electron withdrawing oxoammonium salts

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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