An Efficient Catalytic Oxidation of p-Alkoxypenols to p-Quinones Using Tetrabutylammonium Bromide and Oxone

Journey Describing Applications of Oxone in Synthetic Chemistry

“…p -Quinones are integral structural components of a large number of natural products and have proven to be the most useful synthetic intermediates. − Yakura et al , demonstrated a novel catalytic hypervalent iodine oxidation of phenol derivatives using catalytic amounts of 4-iodophenoxyacetic acid and Oxone as a co-oxidant. p -Alkoxyphenols were oxidized to the corresponding p -quinones in aqueous acetonitrile in excellent yields (Scheme ).…”

Unique Remote Regiocontrol by an N‐Oxide Group in the Synthesis of Isocaulibugulones A, B, C, and D

“…The use of NCS or NBS, for example, leads to polyhalogenation in both rings beyond the quinone production [18,25] . The use of CAN, [26,27] DMD, [28] PIFA, [29] or Oxone [30] was also ineffective. The oxidative amination proved to be dependent on temperature and the solvent used.…”

A Chemo-Enzymatic Expeditious Route to Racemic Dihexanoyl (2<i>R</i>*,3<i>R</i>*,4<i>R</i>*)-Dehydroxymethylepoxyquinomycin (DHMEQ), the Precursor for Lipase-Catalyzed Synthesis of the Potent Nuclear Factor-κB Inhibitor, (2<i>S</i>,3<i>S</i>,4<i>S</i>)-DHMEQ

“…Oxone ® (potassium peroxymonosulfate) with a catalytic amount of tetra-n-butylammonium bromide 4) afforded 7a in 60% yield (four steps, from 5a, Chart 2) as yellow prisms (mp 123.8-124.0°C). Therefore, the use of expensive hypervalent iodine oxidant could be avoided.…”