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Investigation of the action of selected oxidizing agents on D-Mannitol-1,2,3,5,6,-pentanitrate

University of British Columbia

The oxidation of D-Mannitol-1,2,3,5,6-pentanitrate by a selection of non-specific oxidants was investigated under acidic, basic and neutral conditions. Results of preliminary experiments led to further study of the action of chromium trioxide in acetone solution on the pentanitrate. Short term oxidation with this mixture yielded a syrupy product which on hydrogenation gave a further, optically Inactive syrup which did not give a positive test with Pacsu's ketose reagent or with Fehling's solution. When the reaction was allowed to go to completion, a white crystalline compound, which did not reduce Fehlings solution was isolated from the oxidation mixture. This compound, which was not identified, yielded D-mannitol on hydrogenation but differed in physical properties and infra-red spectra from D-Mannitol-1,2,3,5,6,-pentanitrate, D-Mannitol hexanitrate and isomannide dinitrate.

Text

2012-02-08

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http://hdl.handle.net/2429/40561

Chemistry

University of British Columbia

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