Rearrangement of 3-Acyl Derivatives of L-Ascorbic Acid
作者:
Jose Cabral,
Paul Haake,
Karl Kessler,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 9
页码: 1321-1329
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002356
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Evidence of rearrangement of 3-acyl derivatives of ascorbic acid to 2-acyl derivatives has been found for carbon and phosphorus acyl groups. The observations are consistent with intramolecular rearrangement through a cyclic intermediate in which the acyl group is bonded to both the 2- and 3-oxygen atoms of ascorbic acid. A rate of rearrangement has been measured for the 3-diphenylphosphinate ester. Calculated results indicate an increase in negative atomic charge at O-2 in the 3-acyl esters but a decrease in the charge of O-3 in the 2-acyl esters.
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