Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose
Publication type: Journal Article
Publication date: 1988-12-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
The sulfuric acid-catalysed reaction of 1,6-anhydro-β- d -glucopyranose in 1-butanol at 80° gave butyl α- and β- d -glucopyranoside as the sole products. The initial kinetic α/β ratio was 1.5, and the final α/β 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 1 C 4 - B o,3 interconversion of 1,6-anhydro-β- d -glucopyranose and a 4 H 3 -like oxycarbonium species.
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Straatho A. J. J. et al. Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose // Carbohydrate Research. 1988. Vol. 184. pp. 163-169.
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Straatho A. J. J., Vrolijk J. M., van Bekkum H., Kieboom A. P. G. Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose // Carbohydrate Research. 1988. Vol. 184. pp. 163-169.
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TY - JOUR
DO - 10.1016/0008-6215(88)80014-4
UR - https://doi.org/10.1016/0008-6215(88)80014-4
TI - Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose
T2 - Carbohydrate Research
AU - Straatho, Adrie J J
AU - Vrolijk, Johannes M
AU - van Bekkum, Herman
AU - Kieboom, Antonius P G
PY - 1988
DA - 1988/12/01
PB - Elsevier
SP - 163-169
VL - 184
SN - 0008-6215
SN - 1873-426X
ER -
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@article{1988_Straatho,
author = {Adrie J J Straatho and Johannes M Vrolijk and Herman van Bekkum and Antonius P G Kieboom},
title = {Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose},
journal = {Carbohydrate Research},
year = {1988},
volume = {184},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/0008-6215(88)80014-4},
pages = {163--169},
doi = {10.1016/0008-6215(88)80014-4}
}