Weerman degradation

Weerman degradation

The Weerman degradation is an organic reaction in carbohydrate chemistry in which an aldonamide (derived from an aldonic acid) is degraded by sodium hypochlorite forming a new sugar with one less carbon. The reaction is named after R.A. Weerman [R. A. Weerman, Rec. Trav. Chim., 37, 16 (1917).]

The reaction mechanism is that of the related Hofmann degradation. One study demonstrated the direct oxidation of glucose to arabinose by the same sodium hypochlorite skipping the aldonic acid and aldoamide steps. ["Preparation of D-Arabinose from D-Glucose with Hypochlorite"Roy L. Whistler and Richard Schweiger J. Am. Chem. Soc.; 1959; 81(19) pp 5190 - 5192; DOI|10.1021/ja01528a042]

References

ee also

*Curtius rearrangement
*Hofmann degradation
*Ruff-Fenton degradation
*Wohl degradation


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