ORCID: https://orcid.org/0000-0002-0534-3585 and Taylor, Mark S.
ORCID: https://orcid.org/0000-0003-3424-4380
(2024):
On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals.
In: Organic & Biomolecular Chemistry, Vol. 22, No. 16: pp. 3225-3229
[PDF, 882kB]
Abstract
A computational study of the mechanism of hydrogen atom transfer-induced carboxylate elimination from monoacylated 1,2-diol groups in pyranosides is presented. A comprehensive analysis of the 1,2-migration, elimination and fragmentation pathways reveals that concerted elimination via a 7-membered, hydrogen-bonded transition state is favored. Relative rates of elimination inferred from an intramolecular competition experiment are consistent with the trends obtained from the calculations.
Item Type: | Journal article |
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Faculties: | Chemistry and Pharmacy > Department of Chemistry |
Subjects: | 500 Science > 540 Chemistry |
URN: | urn:nbn:de:bvb:19-epub-119776-3 |
ISSN: | 1477-0520 |
Language: | English |
Item ID: | 119776 |
Date Deposited: | 01. Aug 2024, 07:10 |
Last Modified: | 01. Aug 2024, 07:10 |