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THE ACTION OF HYDROXYLAMINE ON METHYL ALPHA- AND BETA-D-GLUCOPYRANOSIDE TETRANITRATE IN PYRIDINE

 

作者: L. D. Hayward,   C. B. Purves,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1954)
卷期: Volume 32, issue 1  

页码: 19-30

 

ISSN:0008-4042

 

年代: 1954

 

DOI:10.1139/v54-004

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

The methyl glucoside tetranitrates reacted vigorously at room temperature with an excess of hydroxylamine base dissolved in anhydrous pyridine. Gas consisting of 91% nitrogen and amounting to 1.25 to 1.3 moles per mole was evolved within 20 min. and only a little more during the next 12 hr. Approximately 1.35 moles of nitrate groups in the original tetranitrate had been replaced by hydroxyl groups, for the most part at least without Walden inversions or other change, because hydrogenation of the sirupy product reduced it in more than 80% yield to crystalline methyl glucoside. The product from methyl-β-glucoside tetranitrate consisted of the 2,3,6-trinitrate (28%), the 3,6-dinitrate (17%), and an unidentified trinitrate (8%) which might have been a mixture.The structures of the first two compounds were confirmed by preparing the fully methylated derivatives, denitrating the latter, and identifying the resulting known, partly methylated methyl-β-glucosides. New syntheses of methyl-β-glucoside-3,6-dinitrate, methyl 2,4-dimethyl-β-glucoside, and methyl-4-methyl-β-glucoside were found.

 

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