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Volumn 63, Issue 25, 1998, Pages 9367-9374

Oxoammonium salts. 6. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1- oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETYLAMINO 2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXOAMMONIUM PERCHLORATE; AMMONIUM DERIVATIVE; OXOAMMONIUM SALT; PIPERIDINE DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG;

EID: 0032509230     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981322c     Document Type: Article
Times cited : (156)

References (63)
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    • note
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    • note
    • One equiv of 2-octanol was allowed to react with 0.5 equiv of salt, and the 2-octanol:2-octanone ratio was determined by GC. The theoretical result was compared with the actual result to determine salt purity.
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    • The salt is soluble in cold water to the extent of about 2 g/100 mL. It can be recrystallized by being dissolved in about 6 parts of rapidly boiling water followed by rapid cooling. It reacts slowly with boiling water, as has been noted for other oxoammonium salts (Endo, T.; Miyazawa, T.; Shihashi, S.; Okawara, M. J. Am. Chem. Soc. 1984, 106, 3877).
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    • note
    • Ethanol reduces the salt, 1, to the hydroxyamine salt, 2, which is deprotonated by the base to free hydroxyamine which reacts with 1 to give nitroxide (see Scheme 2).
  • 61
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    • note
    • 2O.
  • 62
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    • note
    • It is best to add the oxidant last to the substrate and solvent. In at least two cases, furane derivatives and dimethyl sulfoxide, the reaction between salt and pure material was very vigorous.


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