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Turner, Julia A.; Zipse, Hendrik ORCID logoORCID: https://orcid.org/0000-0002-0534-3585 and Taylor, Mark S. ORCID logoORCID: 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.

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