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Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds

Gonzalez, C.C. and Kennedy, A.R. and Leon, E.I. and Riesco-Fagundo, C. and Suarez, E. (2001) Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds. Angewandte Chemie, 40 (12). pp. 2326-2331. ISSN 0044-8249

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Abstract

The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through β-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis.

Item type: Article
ID code: 1242
Notes: Related item: http://strathprints.strath.ac.uk/22673/ Non-duplicate
Keywords: carbohydrates, chirality, halides, iodine, radical reactions, Chemistry, Medicine(all)
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Faculty of Engineering > Electronic and Electrical Engineering
Related URLs:
Depositing user: Catriona Mccallum
Date Deposited: 12 Jun 2006
Last modified: 04 Sep 2014 10:42
URI: http://strathprints.strath.ac.uk/id/eprint/1242

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