Abstract
THE action of alkaline hypochlorite upon fully methylated hexonic and pentonic acid amides, using the Weerman procedure1, results in the formation of cyclic urethanes2. Haworth, Peat and Whetstone3, using this reagent, claimed the direct conversion of 3 : 5 : 6-trimethyl-d-gluconamide (which possesses a free α-hydroxyl group) to a 2 : 4 : 5-trimethyl arabinose, isolated as a syrup, to which a straight-chain aldehydic structure was ascribed.
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References
Weerman, R. A., Rec. trav. Chim., 37, 16 (1917).
Irvine, J. C., and Pryde, J., J. Chem. Soc., 1045 (1924). Pryde, J., Hirst, E. L., and Humphreys, R. W., J. Chem. Soc., 348 (1925). Humphreys, R. W., Pryde, J., and Waters, E. T., J. Chem. Soc., 1298 (1931).
Haworth, W. N., Peat, S., and Whetstone, J., J. Chem. Soc., 1975 (1938).
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DODGSON, K., PRYDE, J. Action of Alkaline Hypochlorite on 3 : 5 : 6-Trimethyl-d-gluconamide. Nature 170, 35–36 (1952). https://doi.org/10.1038/170035c0
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DOI: https://doi.org/10.1038/170035c0
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