1. ChemInform Abstract: Sodium Hypochlorite Pentahydrate (NaOCl·5H2O) Crystals; An Effective Re-Oxidant for TEMPO Oxidation
- Author
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Tomotake Asawa, Yukihiro Sugiyama, Yoshikazu Kimura, Tomohide Okada, Masayuki Kirihara, and Toshiaki Iwai
- Subjects
Steric effects ,Nitroxyl radicals ,chemistry.chemical_compound ,Aqueous solution ,Chemistry ,Sodium hydroxide ,Sodium hypochlorite ,Sodium ,Oxidizing agent ,chemistry.chemical_element ,General Medicine ,Catalysis ,Nuclear chemistry - Abstract
The novel oxidant of sodium hypochlorite pentahydrate (NaOCl·5H2O), which is now available for industrial and laboratory use has several advantageous properties. The crystalline material has 44% of NaOCl, contains minimal sodium hydroxide and sodium chloride, and the aqueous solution indicates pH 11–12. Herein, NaOCl·5H2O crystals are examined for use as an oxidant for primary and secondary alcohols, with or without nitroxyl radicals, in the presence or absence of phase-transfer catalysts. The pentahydrate crystals alone (without nitroxyl radicals) demonstrate a powerful oxidizing ability, converting secondary alcohols to the corresponding ketones. In the presence of TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl) or 1-Me-AZADO (1-methyl-2-azaadamantane N-oxy radical), sterically hindered secondary alcohols are oxidized without pH adjustment. A proposed mechanism for the oxidation is discussed.
- Published
- 2016
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