December 2000
Intermediate to advanced
416 pages
11h 19m
English
Content preview from Electrochemical Reactions and Mechanisms in Organic Chemistry
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CHAPTER 8
OXIDATION OF ALCOHOLS, AMINES AND AMIDES
Nitroxyl Radicals
Oxidation of dialkylhydroxylamines with no α-hydrogen substituents proceeds in two reversible one-electron steps. The intermediate nitroxyl radical 2 is the stable species under ambient conditions. The more highly oxidised form 1 finds use as
a reagent for the oxidation of alkanols to the carbonyl compound. Standard reduction potentials for these species are give in Table 8.1.
TABLE 8.1
Redox behaviour of nitroxyl radicals in acetonitrile with tetraethylmmonium perchlorate as electrolyte.
Footnotes:
(a) Data from [9], adjusted to see using data for oxidation of 2,2,6,6-tetramethylpiperidinyl-1 ...
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