Weerman reaction

Treatment of D-glucoascorbic acid (XV) with diazomethane gives a 2,3-dimethyl derivative (LXXIX) and this upon repeated treatment with silver oxide and methyl iodide yields 2,3,5,6,7-pentamethyl-D-glucoascorbic acid (LXXX). Ozonization of the latter followed by hydrolysis gives oxalic acid and 3,4,5-trimethyI-D-arabonic acid (LXXXI). This acid was shown to possess a free hydroxyl group at C2 by reason of the fact that the amide of LXXXI gives a positive Weerman reaction for a-hydroxy amides, i.e., when the amide is treated with sodium hypochlorite, sodium isocyanate is produced, the latter being identified by... 

In the Weerman reaction, treatment of an amide with sodium hypochlorite and alkali leads to the formation of a sugar lower in the series in this way a hexonamide is converted into a pentose sugar. The first stage in this transformation is the formation of the corresponding iso-... 

Trimethyl-D-arabofuranose (XXV) has been prepared by the degradation of 2,3,4,6-tetramethyl-D-gluconamide (XXIII) by the action of sodium hypochlorite (Weerman reaction), the cyclic urethane (XXIV) undergoing hydrolysis with dilute sodium hydroxide solution in the cold.80... 

This reaction is related to the Weerman Reaction, Wohl Degradation, and Fenton... 

The application of the Hofmann and Curtius rearrangement to the preparation of 2-thienvb)cetaldehyde (55) was studied, utilizing the degradation employed by Weerman. These reactions could be represented as follows ... 

WEERMAN DEGRADATION. Formation of an aldose with one less carbon atom from and aklonic acid by a Hoffmann-type rearrangement of the corresponding amid. This is a general reaction of a-hydroxycarboxylic acids. 

The Weerman degradation was employed in one of the first preparations of dialdoses, namely of n-f/ireo-tetrodialdose, using the diamide of D-glucaric acid as starting material. An inosose has been degraded to a pentodialdose by way of its disulfone and the Nef reaction, transformation of a 6-deoxy-... 

This reaction is related to Curtius Rearrangement, Lossen Rearrangement, Schmidt Reaction, Weerman Degradation, and Wolff Rearrangement. 

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