Summary
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1.
2,3,4-Tri-O-methyl-1,6-anhydro-D-mannopyranose reacts with sodium in liquid ammonia under the conditions that have been found to be optimum for trimethyllevoglucosan with formation of phenol in 15–17% yield. This is only one-third of the yield in the analogous reaction with 2,3,4-tri-O-methyl-1,6-anhydro-D-gluco-, -D-ido-, and -D-gulo-pyranoses and only one-half of the yield in the reaction with 2,3,4-tri-O-methyl-1,6-anhydro-D-galactopyranose.
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2.
In the reaction of 1,6-anhydrides of hexoses with sodium in liquid ammonia, apart from monohydric phenol, about 10% of a mixture of three dihydric phenols (resorcinol, pyrocatechol, and resorcinol monomethyl ether) is formed.
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The authors thank Prof. H. Erdtmann and Dr. Meyer (Stockholm) for the provision of ivory nuts.
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Shorygina, N.N., Davydova, G.V. Dihydric phenols obtained in the carbocyclization of 1,6-anhydrides of D-hexoses. Russ Chem Bull 11, 1966–1968 (1962). https://doi.org/10.1007/BF00921356
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DOI: https://doi.org/10.1007/BF00921356