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58
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20644435280
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note
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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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59
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0001564429
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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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60
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20644464899
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note
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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).
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61
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20644447513
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note
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2O.
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62
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20644436180
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note
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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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0000206852
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