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The Acetolysis of the Methyl D-Glucopyranoside Tetraacetates
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The acetolyses of the alpha and beta methyl D-glucopyranoside tetraacetates in 1:1 acetic acid - acetic anhydride 0.5M with respect to sulphuric acid at 25°C were followed polarimetrically and by isotopic dilution analysis. The data shows that the reaction of the α-anomer proceeds as follows: H O- O- AcCOCH3 k1-> HCOCH3 k1-> AcCOCH k2-> HCOAc | | | k1 = 0.0075, k2 = 0.0306, k3 = 0.0043, k4 = 0.0007 min^-1 whereas that of the β-glucoside proceeds as follows: k5 = 0.0212, k6 = 0.041 min^-1 The course of the latter reaction is rationalized on the basis of an ion-pair …

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