On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals

Turner, Julia A.; Zipse, Hendrik und Taylor, Mark S. (2024): On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals. In: Organic & Biomolecular Chemistry, Vol. 22, No. 16: pp. 3225-3229

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
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1477-0520
• Language: English