Carbohydrates nitration

Nitrogen-containing bases have been used to bring about partial deprotection of carbohydrate nitrates. Considerable selectivity was achieved in the reaction245 of 6-0-acetyl-l,2-0-isopropylidene-a-D-glucofuranose 3,5-dinitrate in benzene solution with a 30% solution of dimethylamine in ethanol, from which 1,2-O-isopropylidene-a-D-glu-cofuranose 5-nitrate was isolated in 47% yield. 

Although hydrazine hydrate in ethanol is effective in achieving denitration of carbohydrate nitrates,243,244 the reagent showed little selectivity in its reactions244 with the 2,3-dinitrates of methyl 4,6-O-ben-zylidene-a- and methyl 4,6-0-ethylidene-a- and -/3-D-glucopyranoside. 

This account, supplementary to the recent review of the chemistry of the nitrates of simple aliphatic alcohols, describes the preparation, properties, and reactions of carbohydrate nitrates, but deals neither with the important physical properties nor with the thermal and explosive decompositions of polysaccharide (especially cellulose) nitrates. 

Esterification with mixed acids is often suitable for the preparation of carbohydrate nitrates, but sometimes a less vigorous method is required. For this purpose, a solution of anhydrous nitric acid in chloroform was introduced by Koenigs and Knorr and found suitable for preparing... 

The characteristic frequencies of some common substituent groups, such as C=0, NH, S=0, and benzene ring, were tabulated in the earlier review. Carbohydrate nitrates and sulfonates have since been studied in detail and another useful correlation that enables the methoxyl group to be detected by means of a characteristic C—H stretching band at 2882... 

Cleavage of nitro groups from carbohydrate nitrates... 

Solution combustion synthesis makes use of salts, such as nitrates, metal sulfates and carbonates, as oxidants and, reducing reagents, fuels such as glycine, sucrose, urea, or other water soluble carbohydrates. Nitrate acts as an oxidizer for the fuel during the combustion reaction. The powder can be a pyrolysed product of a single phase, but usually it is a combination of metal oxides and in some cases it needs subsequent heat treatment to form single-phase products, which are usually the results required in this process. 

Carbohydrate nitrates have considerable importance as explosives 127). Cellulose nitrate, of a high degree of nitration (approximately 2.5 groups per anhydro-D-glucose unit), plasticized with glycerol trinitrate, is cur-... 

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