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UBC Theses and Dissertations

The synthesis of allitol hexanitrate Bowering, William David Samuel


Two methods for the synthesis of D-allose from D-ribose, the nitromethane condensation and the cyanohydrin synthesis, were investigated. The nitromethane condensation was first tested with D-arabinose and crystalline derivatives of D-mannose and D-glucose were obtained. In the nitromethane condensation with D-ribose, it was, found that a considerable portion of the D-ribose did not react. A partial separation of the resulting nitroalcohols from the unreacted D-ribose was achieved on an adsorption chromatography column. Application of the cyanohydrin synthesis to D-ribose yielded γ -D-allonolaetone which was reduced to D-allose and then to allitol by sodium amalgam and Raney nickel, respectively. The pure allitol which was obtained in crystalline form was characterized by the melting point, analysis, and acetylation to the known, crystalline hexaacetate derivative. Crystalline allitol hexanitrate was prepared by the nitration of allitol with a mixture of fuming nitric and sulfuric acids or with a mixture of fuming nitric acid and acetic anhydride, and is now reported for the first time. A qualitative experiment indicated that allitol hexanitrate reacted more slowly with dry pyridine at room temperature than the corresponding D-mannitoI derivative and produced no gaseous product.

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