正丁醛和某些d-葡萄糖醇衍生物在酸催化下形成单缩醛

T. G. Bonner, E. J. Bourne, P. J. V. Cleare, R. Cole, D. Lewis
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引用次数: 4

摘要

正丁醛与(a) 1-脱氧-d -葡萄糖醇的酸催化缩合反应生成2,3-缩醛作为动力学控制产物和2,4-缩醛作为热力学控制产物,(b) 2-脱氧-d -葡萄糖醇生成1,3-缩醛作为动力学控制产物和3,4-缩醛(s)作为热力学控制产物,(c) 3- o -甲基-d -葡萄糖醇生成2,4-缩醛作为整个反应的主要产物。在酸性水溶液中,没有证据表明1,3- o -丁基-2-脱氧-d -葡萄糖醇发生分子内转化;相反,在合成3,4-缩醛之前,多元醇和醛发生了实质性的水解。
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Acid-catalysed formation of monoacetals from n-butyraldehyde and certain D-glucitol derivatives
Acid-catalysed condensation of n-butyraldehyde with (a) 1-deoxy-D-glucitol yields a 2,3-acetal as a kinetically controlled product and the 2,4-acetal as the thermodynamically controlled product, (b) 2-deoxy-D-glucitol yields the 1,3-acetal as the kinetically controlled product and the 3,4-acetal(s) as the thermodynamically controlled product, and (c) 3-O-methyl-D-glucitol yields the 2,4-acetal as the predominant product throughout the reaction.In aqueous acid there is no evidence that 1,3-O-butylidene-2-deoxy-D-glucitol undergoes intramolecular conversion; instead substantial hydrolysis to the polyol and aldehyde occurs before the synthesis of the 3,4-acetal(s).
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Kinetics and mechanism of electrophilic substitution of heteroaromatic compounds. Part XXIII. Acid-catalysed hydrogen exchange of quinoline, isoquinoline, and their N-oxides Dielectric relaxation and dipole moments of substituted pyrroles Free-radical addition to olefins. Part VII. Addition of trichloromethyl radicals to chloro-olefins Primary hydrogen isotope effects on the rate of ionization of nitroethane in mixtures of water and dimethyl sulphoxide The conformational analysis of saturated heterocycles. Part XXXV. 1-Phenoxymethyl-3,4-dihydroisoquinolines
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