TEMPO-Mediated Oxidation of Alcohols
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[21] Although
chromium(VI)-based
polymer-bound-re-
agents[4a,5,16a] are strong oxidants with comparable reac-
tivity to the reagents described in this report, the poly-
styrene-based versions tend to decompose which results
in substantial contamination of the solution and thus
work-up problems. On the other hand, it was observed
that immobilisation of the permanganate(VII) anion to
exchange resins[16a] leads to an oxidant which allows
one to transform activated allylic and benzylic alcohols
to the corresponding aldehydes but fails to effectively
oxidise non-activated secondary alcohols. The counter
cation can be made responsible for the reduced reactivity
of the permanganate exchange resin. In fact, when potas-
sium permanganate is immobilised through polystyrene-
supported polyoxyethylene (crown ether approach) an
immobilised oxidant is obtained which is able to oxidise
´
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Adv. Synth. Catal. 2005, 347, 1423–1434
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