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Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose

✍ Scribed by Adrie J.J. Straatho; Johannes M. Vrolijk; Herman van Bekkum; Antonius P.G. Kieboom

Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 379 KB
Volume: 184
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(88)80014-4

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✦ Synopsis

The sulfuric acid-catalysed reaction of 1,6-anhydro+D-glucopyranose in lbutanol at SO" gave butyl a-and P-D-glucopyranoside as the sole products. The initial kinetic alp ratio was 1.5, and the final a//3 ratio upon equilibration was 2.7. The four pseudo-first-order reaction rate constants involved have been determined. Conformational studies showed that the reaction probably proceeds via a lC,-B,,X interconversion of 1,6-anhydro-p-D-glucopyranose and a 4H,-like oxycarbonium species.

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