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- W1908546927 abstract "[31785-68-9] C8H14NO (MW 140.20) InChI = 1S/C8H14NO/c10-9-7-3-1-4-8(9)6-2-5-7/h7-8H,1-6H2/t7-,8+ InChIKey = SZAKAAGHPLUEPM-OCAPTIKFSA-N (stable nitroxyl radical, highly efficient organocatalyst for the oxidation of both primary and secondary alcohols to aldehydes and ketones, respectively; trapping agent for carbon radicals) Solubility: soluble in a wide variety of common organic solvents such as CH2Cl2, CHCl3, CH3CN, benzene, fluorobenzene, n-hexane, and cyclopentane. Form Supplied in: red solid. Preparative Method: the title reagent can be prepared in three steps commencing with the decarboxylative double Mannich condensation of acetonedicarboxylic acid with glutaraldehyde and ammonia. Hydrazine reduction of the resultant bicyclic amino ketone using the Huang–Minlon modification of the Wolff–Kishner reduction followed by oxidation of the amine function with cat Na2WO4 and urea hydrogen peroxide (UHP) furnished ABNO as a red solid in 42% overall yield after purification by silica gel column chromatography (eq 1).1 (1) Purification: checked by TLC; purified by column chromatography on silica as needed; analytical samples can be prepared by sublimation: phase change 50 and ca. 85 °C, mp 126–129 °C. Handling, Storage, and Precautions: care should be taken in handling this free radical reagent due to potential toxicity; should be stored in dark." @default.
- W1908546927 created "2016-06-24" @default.
- W1908546927 creator A5036404201 @default.
- W1908546927 date "2010-10-15" @default.
- W1908546927 modified "2023-09-26" @default.
- W1908546927 title "9-Azabicyclo[3.3.1]nonane-N-oxyl" @default.
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- W1908546927 doi "https://doi.org/10.1002/047084289x.rn01209" @default.
- W1908546927 hasPublicationYear "2010" @default.
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